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The Top 15 Saddest Moments in MMA History

Combat sports can draw on human emotion like no other sports can - the risks and rewards involved are so much more primal, the dangers so much more real, they truly offer the highest of highs and the lowest of lows.

Recently we looked at some of those highs in detail, but what about the lows?

Though Fight Island has certainly kept us entertained for the last few weeks, it has also reminded us of how depressing the sport can be.

At UFC 251, for the better part of 15-minutes former featherweight king Jose Aldo went back to his roots and showed that he was more than capable of not only holding his own against the current top talent, but even of beating them, only for his cardio to fail him and subsequently derail his bantamweight title hopes as Petr Yan poured on the pressure late.

The loss wouldn't have been so bad if it weren't for the horrific judgement shown by referee Leon Roberts, who in the fifth round, let Aldo take upwards of one hundred unanswered strikes as Aldo's busted open face spewed blood on the canvas while he knelt helplessly on the floor, crippled by exhaustion as his corner and the referee stood idly by and watched him take unneccessary punishment.

Last weekend we witnessed longtime fan favourite Joseph Benavidez take one of the most vicious one-round beatings in MMA history in what was to be his last attempt at a UFC title.

The Team Alpha Male standout has been the perennial top contender, first in bantamweight then at his true home of flyweight since the division was introduced in 2012, never dropping below the top three in the rankings and only ever losing to champions Dominick Cruz and Demetrious Johnson (save for an extremely controversial loss to Sergio Pettis).

Despite holding a win over Henry Cejudo, Benavidez never got a shot at Cejudo's title as the former champion opted to fight a descending bantamweight and then move up in weight classes - instead, he finally earned his third crack at UFC gold opposite Deiveson Figueiredo earlier this year for the vacant strap.

The fight was shrouded in controversy as Figueiredo missed weight, then an accidental headbutt in the second round that went unnoticed by the referee led to a knockout loss for Benavidez - with Figueiredo inelligible to win the title because he missed weight and the controversy surrounding the finish, Benavidez was given a shot at redemption last Saturday.

Most expected the fight to go Figueiredo's way, especially given that he was in better shape and made weight this time, but few expected the extremely vicious way in which Benavidez would lose.

Figueiredo dropped Benavidez not once, not twice, but three times in the opening round, securing two tight rear-naked chokes to try and finish the tough vet that Benavidez somehow managed to survive. After the third knockdown and another locked-in rear-naked choke, Benavidez was finally finished and went unconscious as the iron-willed contender refused to tap.

If those brutal bouts aren't enough to get you feeling depressed, don't worry, we've got you covered - here are 15 of the saddest moments in MMA history.

Note: this list is purely speaking about in-cage moments and as such does not include things such as deaths, illnesses, injuries, etc. that occurred outside of competition.

15. Urijah Faber getting demolished by Petr Yan

The first entry on this list comes at the expense of Joseph Benavidez's mentor, Urijah Faber.

Fans of the "California Kid" considered themselves lucky when the longtime fan favourite announced his retirement in 2016 - while seeing a legend in the sport hang up their gloves is always bittersweet, unlike most fighters Urijah Faber had chosen to finish his illustrious career before he had sustained the excessive damage and string of knockout losses most of his peers suffer in their waning years.

Though his retirement fight showed he was still more than capable of putting on a show and competing with solid competition, Faber had clearly declined in recent years and simply wasn't the perennial contender he once was - despite this, he had still managed to avoid taking excessive punishment while competing against top flight competition and his only finish loss in the last eight years had been a highly controversial early stoppage against Renan Barao.

Faber had unsurprisingly remained in the gym throughout his retirement and teased that he could return for the "right fight", but that idea seemed to fizzle out as time went on - until 2019.

Out of nowhere Urijah announced that he was coming out of retirement to make another title run, accepting a fight with the vastly younger prospect Ricky Simon.

Reaction to the news was rather mixed - many thought the 40-year-old would simply not be able to compete with the extremely strong and athletic Simon, though savvy fight fans knew Simon's rather lacking (at the time) striking skills and porous defense offered a clear path to victory for Faber even at his advanced age, especially given that power tends to be the last thing to go in an aging fighter.

Faber would ignite his hometown Sacramento crowd by smashing the highly touted prospect in just 46 seconds, announcing to the stacked bantamweight division that the California Kid wasn't done terrorizing them just yet.

The thrilling victory certainly made for a good story, but some were fooled into thinking that Faber would be able to still compete with the top contenders in the shark tank that is the 135-pound division.

In truth, even at 40 Faber is still more than capable of beating most bantamweight fighters on the planet - earlier in his career however he would often come up short against the truly elite in the division, and even though he hadn't accrued a huge amount of damage in his career, his ability to absorb punishment had understandably diminished with age and that would spell disaster against a truly top-tier opponent at this stage in his career, especially as his reflexes and speed continued to decline.

Regardless, Faber's win and name value earned him a top contender and a title shot should he win - the only problem was that he'd have to go through an absolute killer in Petr Yan to do it.

Even fans that had picked Faber to beat Ricky Simon dreaded this fight when the time came for the two to enter the Octagon.

Petr Yan was a 13-1 powerhouse with a strong grappling background, slick boxing and heavy hands combined with a relentless pace and iron chin. Although Faber would certainly have an experience advantage, Yan had cut his teeth fighting extremely talented competition in Russia and had defeated all five of his UFC opponents, including vets like John Dodson and top ten staple Jimmie Rivera.

The 26-year-old Russian would not only sport a youth advantage, but his style would have made him an extremely tough matchup for Urijah even in his prime - at 40 years of age, Faber would need a miracle just to survive let alone win against someone like Yan.

Faber started off well when the two locked horns at UFC 245 late last year, his trademark speed still holding up all these years later (at least for the opening minutes). Faber scored with strikes of his own and managed to avoid damage for the most part, with some even scoring the competitive round in Faber's favour.

Yan however is known to be a slow starter - he's a textbook swarmer, a striker that relentlessly walks down his prey and continues to open up more and more as a fight goes on, wearing down his victims with vicious combinations until they break.

The second round was what all of Urijah's fans had feared - and then some.

Yan began to find his range, smashing Faber with brutal combinations and savage knees as Faber looked to change levels. Urijah would get dropped twice in the middle frame, showing off his remarkable toughness and fighting spirit by somehow managing to survive the hellacious onslaught.

It was a brutal beatdown and while Faber got through the round by the skin of his teeth, the writing was on the wall.

Years ago, the supremely conditioned Faber would have had a chance to mount a come back in the third round after recovering on his stool; at his age however, no matter how well conditioned an athlete is one simply cannot recover from that kind of punishment in such a short amount of time.

Of course, Urijah would never back down or give up and so he opted to go out on his shield. Less than a minute into the final stanza, Yan attempted a knee as Faber backed out of the clinch; realizing the knee would come up short, Yan instead flicked out his leg and turned it into a kick, catching Faber with his foot and putting the legend down for the third and final time.

The brutal knockout may not have been unexpected, but it was nonetheless heartbreaking for MMA fans around the world.

Faber had seemingly spared his fans from seeing him take unneccessary damage and retired at the right time, only to fall into the same trap that befalls almost every fighter in combat sports just a few years later.

He took more punishment in less than eleven minutes against Yan than he had in most of his career combined. In fact, in his entire WEC/UFC career (which spanned over a decade and 29 fights), Faber had been knocked down just four times, yet he was knocked down three times in the span of about six minutes at UFC 245.

It was a sad reminder that age catches up to every fighter and that sometimes, toughness and heart just earns you a worse beating.

14. Chris Weidman getting slaughtered in New York

A New York native who had been a prominent supporter of the UFC's efforts to legalize the sport in the holdout state of New York, it was hardly a surprise that the former champion would earn himself a high-profile fight in the UFC's first-ever trip to the famous Madison Square Garden Arena.

After an injury forced him to pull out of an instant rematch with Luke Rockhold for the middleweight title he had just lost, Weidman would look to bounce back from his first career loss by taking on fellow top contender Yoel Romero at UFC 205.

The 11-1 Cuban Olympic silver medalist was riding a seven fight winning streak inside the Octagon with five brutal knockouts to his credit. The contendership bout was one of the most highly anticipated fights on the historic card, an event which featured a whopping three title fights.

The fight was going according to plan through the first two rounds - after a strong start from the explosive 40-year-old that secured him the opening stanza, Weidman outworked Romero in the middle frame and sought a similar result in the third which would secure him the workmanlike victory and return his shot at the title.

And then a Cuban missile sucked the air out of the building.

Just seconds into the third round, Romero perfectly timed a flying knee with a double leg attempt from the former champ, a single moment of explosive perfection demolishing Weidman's dreams of attaining victory in front of his home crowd.

Weidman's face brutally smacked into his own knee as he collapsed to the canvas, a few follow up shots just adding to the viciousness of the knockout before the referee had a chance to step in.

As Romero ran around the Octagon to celebrate, the stunned crowd watched while a dazed Weidman sat up, a gash on the side of his head covering his face in blood.

Weidman wasn't the first nor the last man to lose in front of his home crowd, but to see a former champion who had waited so long and fought so hard to get to fight at home and finally had the opportunity to do so, only to lose in such brutal fashion, was certainly a harsh pill to swallow for the once dominant champion.

Even those that weren't Chris Weidman fans couldn't help but feel sorry for the former middleweight king.

His woes in his home state would continue to haunt him as Weidman would go just 1-2 in his three other fights in New York, including a similarly brutal third round knockout loss to Jacare Souza two years later in a fight he was winning.

13. Frankie Edgar getting stopped for the first time

Frankie Edgar is one of the most beloved MMA fighters on the planet and is sometimes referred to affectionately by fans as the "little engine that could".

Always undersized, the natural bantamweight captured the UFC lightweight title after fighting Gray Maynard to a draw in an epic five round war in which Edgar took a disgusting amount of punishment early yet somehow managed to survive and come back to win the latter rounds. He did virtually the exact same thing in an instant rematch but managed to finish his rival in the fourth round with a flurry of punches to avoid another close decision.

After two razor-thin decision losses, Edgar would finally drop down to featherweight (where he was still undersized compared to most of his opposition) and posted an impressive 7-2 record with his only losses coming in decisions to pound-for-pound great Jose Aldo.

The tough New Jersey native would get another crack at the featherweight title after Max Holloway dethroned Jose Aldo in 2017, but an injury put Edgar's shot on hold and instead Max defeated Jose Aldo once again as the former champ stepped up to fill in for Edgar.

Edgar's fight with Holloway would be rescheduled for March 2018, only for Holloway to pull out due to injury a month before the bout - rather than sitting out and waiting for the champion, Frankie followed in Holloway's footsteps and opted to stay active, instead taking on surging prospect Brian Ortega.

A Brazilian jiu-jitsu ace with a penchant for epic comebacks of his own, Ortega's matchup with Edgar thrilled the MMA community and fans expected a back and forth war.

When the two stepped into the cage at UFC 222 however, it quickly became the Brian Ortega show.

Though he carried power and incredible durability, Ortega's striking had largely been rather lackluster in his prior UFC bouts - his eye for openings and timing had proven to be excellent, but his sloppiness and porous defense had most believing Edgar would hold a notable advantage on the feet.

Showcasing vastly improved boxing, Ortega's slick jab, head movement, and size advantage gave Edgar fits early as the savvy vet struggled to get inside on his younger opponent. Edgar's rushes to try and get inside Ortega's reach were soon met with nasty, sharp elbows that rocked the former lightweight king.

A right hook off of a blocked high kick put Edgar on wobbly legs and forced him to desperately try to tie up his aggressor, only to walk right into an uppercut from the pits of hell. Edgar was floored and stopped by strikes for the first time in his 28-fight career.

It was a brutal and devastating loss for the fan favourite, made all the worse by the fact that Edgar shouldn't have taken the fight in the first place - had he simply waited for Holloway to recover from his injury, he'd have fought for the title (a fleeting opportunity for a fighter in a lower weight class at 36 years old); instead, he risked his spot to take on a hungry young challenger and ended up getting viciously knocked out for his trouble.

It served as proof once again that nothing is guaranteed in this sport and sometimes the "safer" option really is better.

12. Kazushi Sakuraba getting demolished by Wanderlei Silva...for the third time

Japanese MMA legend Kazushi Sakuraba could easily have more than one entry on this list - he was a fighter known for his courage and heart just as much as his cunning and skill, a man with the frame of a small middleweight that regularly took on heavyweights and refused to back down to anyone.

As a result, Sakuraba's very impressive early career in PRIDE quickly became one that saw him taking ridiculous amounts of punishment from more powerful strikers when the grappling ace failed to get the fight to the mat.

Coming into PRIDE's 2003 Middleweight (light heavyweight by North American standards) Grand Prix, Sakuraba was just 2-4 in his last six outings; though he did sport a submission victory over Quinton Rampage Jackson, he had been beaten down by Mirko Cro Cop and most recently by the unknown Nino Schembri, in addition to having been stopped twice by one Wanderlei Silva.

When Sakuraba first found himself in the ring opposite Wanderlei Silva, it was in one of the most highly anticipated fights of 2001; although he managed to drop Silva early, Wanderlei proved to be too much for the Japanese star as the Brazilian knocked him out in just 98 seconds.

Their second meeting would come that same year for the PRIDE middleweight title and offered fans the more competitive battle they had anticipated the first time. Sakuraba did well on the mat early and even got Wanderlei in a tight guillotine choke, which Wanderlei countered by slamming his rival to the canvas and breaking his collar bone in the process.

Sakuraba was able to survive the rest of the 10-minute first round despite the injury, but his corner smartly threw in the towel between rounds to avoid any further damage.

Though a third meeting between the two would have been warranted at the time, the idea quickly turned sour as Sakuraba lost two of his next three fights in lopsided fashion, with his lone win coming in a squash match against Gilles Arsene (who?... exactly).

Wanderlei on the other hand had knocked out four of his five opponents since last meeting Sakuraba, the only fighter managing to survive being heavyweight kickboxer Mirko Cro Cop in a special rules bout (as there were no judges for the special bout, it was declared a draw after fifteen minutes of action though Wanderlei had clearly won the fight).

When the two were paired up for the third time in the opening round of PRIDE's 2003 Middleweight Grand Prix, there was little doubt as to who would emerge the victor; Sakuraba was clearly on the decline while Wanderlei had emerged as one of the most feared knockout artists on the planet.

Though he valiantly tried to strike with Silva after failing to take the champion down, Sakuraba would get viciously knocked out midway through the opening round by a vicious combination as he threw a leg kick.

It was an entirely expected yet no less depressing loss, a legend in the sport getting knocked out in brutal fashion in a fight he had no place being in. There's a reason it made the list of trilogy fights that never should have happened.

Aging vets being fed to young lions are certainly a recurring theme in MMA and they're often depressing bouts for longtime fans of the sport, but when it happens with a fighter that's already lost twice to the same hungry young lion, it just becomes disturbing.

11. Antonio Rodrigo Nogueira getting his arm snapped by Frank Mir

By the time Antonio Rodrigo Nogueira made his UFC debut in 2007, he was already a decorated legend in the sport of MMA.

The inaugural PRIDE heavyweight champion had been tapping out his opposition since 1999 and had beaten a who's who of the heavyweight division, from Mirko Cro Cop to Josh Barnett to Fabricio Werdum, the only unavenged losses in his career coming against the man many considered the greatest heavyweight in MMA history, Fedor Emilianenko.

Nogueira would add to his trophy case by submitting Tim Sylvia and capturing an interim UFC heavyweight title early in 2008 before running into fellow submission specialist Frank Mir at UFC 92; rather than engaging in a grappling match against a fellow BJJ black belt as fans had expected, Mir instead chose to keep the fight standing and showcase his improved boxing, picking Nogueira apart on the feet and dropping him three times en route to a second round TKO victory.

Mir became the first man to ever finish the legendarily durable Brazilian that night, and as time went on it became clear that the wars Nogueira had put his body through over the years were starting to catch up to him.

After a win over fellow vet Randy Couture, Nogueira was knocked out for a second time in just over two minutes against future champion Cain Velasquez. He then faced Brendan Schaub, who rocked the Brazilian early before Nogueira turned on the afterburners and felled the glass-jawed former NFL player to get back in the win column.

Mir would see mixed success himself following his victory over Nogueira; immediately following his capture of the interim title, Mir was viciously mauled by his rival Brock Lesnar in an epic grudge match at UFC 100, which inspired Mir to bulk up and add some muscle to his frame in order to compete with the new breed of massive heavyweights.

A much thicker Mir ran through Cheick Kongo before getting smashed in an interim title fight by the brick-fisted Shane Carwin. He then proceeded to engage in a near 15-minute snooze-fest against Mirko Cro Cop then knocked him out in stunning fashion in the last minute of the bout, the impressive finish completely overshadowed by the horrendously dull fight that had occurred up until that point.

A workmanlike decision win over Roy Nelson kept Mir on track but considering the once-exciting heavyweight had now been involved in two dull fights in a row and had lost two of three before that, he was in need of an impressive performance to get himself back into title discussions.

A rematch with Nogueira made sense for all involved, and so the second meeting between the two was set for UFC 140 at the end of 2011.

With a renewed focus on his boxing, Nogueira made the now-lumbering Mir look silly for packing on all that muscle as the aging Brazilian that Mir himself had made look ancient just a few years ago was now regularly beat him to the punch. Later in the opening round, Nogueira popped Mir with a stiff combination that wobbled him and had Frank desperately grabbing onto a leg to attempt a takedown.

Sprawling on Mir, Nogueira peppered his wounded prey with several left hands and had he continued to look for a TKO, given Mir's famously poor instincts on defending himself from strikes when hurt, in all likelihood Big Nog would have walked away the victor. Instead, Antonio looked to become the first man to ever submit Frank Mir as he locked up a guillotine choke and attempted to flip over into mount.

Despite being severely rocked, Mir's survival instincts in the grappling realm proved second-to-none as he rolled out of the submission attempt and wound up on top. Attempting to escape and take Mir's back, Nogueira soon found himself in all sorts of trouble as the American BJJ expert isolated his right arm and brilliantly transitioned into side control to look for a kimura.

As Mir began to crank on Nogueira's arm, the wily vet rolled in an attempt to free himself from the lock, but Mir rolled with him and once again ended up on top before he reefed on his victim's poor arm. Moments later Nogueira's upper arm snapped in half as the result of the most brutal submission in UFC history, forcing Nogueira to tap - but it was clearly too late.

The entire sequence was truly remarkable and it is one of the most sudden and dramatic comebacks you'll ever see in a fight - the fact that Mir could pull off a submission on one of the most decorated Brazilian jiu-jitsu black belts in MMA history moments after being rocked and nearly finished himself is simply absurd.

The submission earned Mir the accolades of being the first man to ever submit Antonio Rodrigo Nogueira (in addition to already being the first man to knock him out) and of being the first and only fighter in the UFC to break the limbs of his opponents with submission holds on two separate occasions (he also famously broke Tim Sylvia's arm years prior to capture the UFC heavyweight title).

As impressive as Mir's win was, it was equally devastating for Nogueira - the nasty fracture of his humerus required a plate with 16 screws to be inserted into his arm to mend the injury.

It was tough to see a legend of the sport be injured in such a gruesome manner and it was made all the more sad for Nogueira fans in knowing that he was so close to achieving victory - had he simply continued hammering away at Mir instead of opting to try and submit him, in all likelihood Nogueira would have picked up an impressive TKO victory instead of having his arm snapped in half like a popsicle stick.

If MMA isn't the most unforgiving sport in the world, I don't know what is.

10. Mirko Cro Cop getting Cro Copped

When Mirko "Cro Cop" Filipovic came over to the UFC in 2007, it was a big deal.

The Croatian kickboxer had made a name for himself as one of the most feared and devastating strikers in mixed martial arts over in PRIDE, racking up an impressive 21-4-2 record which included brutal knockouts over the likes of Igor Vovchanchyn, Mark Coleman, and Wanderlei Silva.

After tearing through the field and winning the PRIDE 2006 Openweight Grand Prix with four first round knockouts, a massive rematch with heavyweight champion Fedor Emilianenko failed to materialize after PRIDE and/or Fedor's management continued to avoid the matchup, and soon Cro Cop would sign a lucrative contract with the UFC instead.

Rather than getting an immediate title shot, the UFC opted to try to build Mirko's popularity in the US before putting him into a championship fight. As a result he made quick work of the undefeated Eddie Sanchez in his UFC debut before squaring off with BJJ black belt Gabriel Gonzaga in a heavyweight title eliminator.

Considered to be primarily a grappler, the burly Gonzaga did sport plenty of knockout power himself as evidenced by his brutal ground and pound and even an impressive superman punch knockout victory in his UFC debut.

Despite being a top prospect, the 7-1 Gonzaga was a massive underdog heading into his heavyweight clash with the legendary Cro Cop; Mirko was clearly one of if not the greatest heavyweights on the planet and if he could stuff the takedowns of men like Josh Barnett, he would surely be able to force Gonzaga into a striking match where his savage kicks (particularly his patented left high kick) and sharp boxing would give him a decided advantage.

At UFC 70, the fight began as expected, with Cro Cop keeping the fight standing and the two heavy hitters squaring off in a tense striking match as a result. And then something happened that no one ever saw coming.

Out of nowhere, thrown with the same no-windup athleticism that Cro Cop had made famous, "Nepao" threw a beautiful head kick that soared right past Mirko's guard, his massive shin clanging off the side of the legendary kickboxer's head.

Mirko was knocked unconscious on impact and collapsed to the canvas, his right leg contorted grotesquely under his limp body.

Cro Cop had gotten Cro Copped.

The "kick heard around the world" stunned the entire MMA world and had fans second-guessing everything they knew about life. How on earth could this happen? How could this lumbering jiu-jitsu player knock one of the most decorated strikers in MMA history out cold with his own favourite strike? Is this some sort of sick joke?

Unfortunately for Cro Cop and his fans, it was not a joke.

The knockout was one of the most brutal in MMA history and effectively shattered Mirko's UFC title aspirations in one fell swoop. For longtime fans of the sport that had watched Cro Cop's legendary career in PRIDE, it was a devastating blow and a bitter pill to swallow, made all the more devastating by the grotesque image of Cro Cop's twisted leg as he laid unconscious in the middle of the Octagon.

9. Junior Dos Santos being booed after his first loss to Cain Velasquez

It was hard not to feel bad for Junior Dos Santos after he lost his heavyweight crown at UFC 155.

The heavyweight knockout artist had been on top of the world for the past year, having knocked Cain Velasquez out in just 64-seconds when they first met a year prior in the main event of the first-ever UFC fight broadcast on Fox.

Although the quick fight wasn't the epic war fans were anticipating, his lovable personality and genuinely kind nature earned him droves of fans during his short-but-sweet title reign, with his lone successful defense being a demolition of Frank Mir while he made a small boy from his hometown's dreams come true by bringing him to Las Vegas to witness his favourite fighter compete cageside.

The story captured the hearts of MMA fans everywhere and confirmed Junior's status as one of the most likeable fighters in the sport, and that's not even taking into account his exciting style and impressive 15-1 record which featured 13 finishes.

When it was time for Junior to face off against Cain Velasquez for the second time, the MMA world finally got to see the epic war they had expected the first time. Unfortunately for Dos Santos, it would come at the expense of his health and his title.

Rather than engaging at range like he had in their first meeting, Cain relentlessly swarmed the Brazilian from the opening bell, landing flurries of strikes to close the distance (even dropping Dos Santos early on) and forcing himself into the clinch repeatedly. From there, Cain relentlessly pursued takedowns while pounding away at his victim, peppering him with punches at every opportunity and constantly forcing him to work.

Junior did an admirable job of defending takedowns and every time Cain did manage to get him down, he would quickly work his way back to his feet - the boxer simply couldn't keep Velasquez away from him however, continuously being peppered with punches as he fought to break free and gain space with which to implement his striking game.

The champion did score some shots of his own, particularly with counters as Cain charged into the clinch, but Velasquez was unstoppable that night and drowned out Dos Santos' offense with his torrential downpour of offense.

As the rounds wore on, Junior's face had turned into a grotesque mess of swelling and blood that had some comparing him to Sloth from The Goonies. Despite the absolute beating he had endured, Junior still came out firing for the fifth and final round, his iron will never wilting under the sea of pressure that he faced. He kept throwing back until the final bell, mustering up every ounce of strength he could to mount a comeback that never manifested.

The brutal loss Junior endured was certainly not one for the faint of heart, but the toughness and unbreakable spirit Dos Santos had showcased to the crowd in Las Vegas was worthy of a standing ovation.

After the lopsided scorecards were read and the victor was interviewed, Joe Rogan turned his mic to Junior. Instead of an appreciative crowd applauding the warrior for his gutsy display of heart and toughness, what happened next was utterly heartbreaking.

As the camera turned to the now-former champion and Rogan asked him about the fight, the Vegas crowd showered the Brazilian with boos. The man had just fought his heart out for 25-minutes, was battered pillar-to-post yet never gave up or stopped trying to win, and he was now being booed by a crowd of people he just gave his all to entertain.

Junior's first words in response were gut-wrenching - "Why are you guys doing that? Why?"

Why indeed.

Rogan quickly inspired a round of applause for Junior to offset the boo-ers, but the initial response was nonetheless an aggravating and extremely sad way to add insult to injury to a man who had just given his all and came up short.

With how genuinely kind and sincere Junior had always been (and continues to be), the pathetic reaction "fans" in Vegas had to him after such a devastating loss remains one of the saddest moments in MMA history to this day.

8. Cain Velasquez getting his chin (and knee) demolished by Francis Ngannou

Cain Velasquez is easily one of the best heavyweights to ever compete in MMA, yet the biggest story of his career has always been his inability to stay healthy.

His 64-second knockout loss to Junior Dos Santos was said to be inspired by an ACL-tear which compromised the champion heading into their massive showdown on Fox, a fight he refused to back out of given it had already been delayed courtesy of a torn rotator cuff and was poised to be one of the most important fights in the sport's history.

The following two years would see Cain stay (relatively) healthy as he earned back his title and emphatically avenged his only loss by beating down Junior in two subsequent meetings. Then Cain's fragile body once again broke down, keeping him out for over 18 months before he would lose his title in dramatic fashion to Fabricio Werdum in Mexico City.

Injuries kept him out for another year before he trounced Travis Browne and announced his triumphant return to healthiness, only to then be sidelined again by various injuries for well over two years.

Early in 2019, Velasquez would finally return to the Octagon to take on feared knockout artist Francis Ngannou.

Despite Cain's laundry list of injuries and his extended layoff, many liked the former champion's chances in the matchup - Ngannou's hype train had been emphatically derailed by the heavyweight champion Stipe Miocic, who smothered Ngannou's offense with a relentless wrestling attack and grinding pace.

If Velasquez was even close to his former self, he should have no problem implementing the exact same gameplan and grinding Ngannou down en route to a lopsided victory.

The problem?

Cain's style of closing the distance has always left him dangerously exposed and has seen him taking big shots on the way in against all of his opponents that were capable strikers. Velasquez would simply accept the damage as a tradeoff for getting the fight to his preferred space, something he had done time and time again in his fights with Junior Dos Santos and even Cheick Kongo, who had nearly knocked Velasquez out multiple times due to Cain running onto his strikes.

Against someone like Francis Ngannou that can generate true knockout power from virtually anywhere, that style is simply suicidal.

It didn't take long for Ngannou to make his power felt as he stuffed a Cain takedown early in their fight, backing himself into the cage in the process. As Velasquez desperately tried to re-shoot in on his legs, Ngannou landed an extremely short right hook that floored Cain, dropping the former champion awkwardly on his leg in the process.

The knockdown blew out Cain's knee and the former champion cried out in agony as Ngannou proceeded to follow up with strikes on his injured foe, knocking Cain in and out of consciousness before the ref could step in and save him.

The entire fight unfolded in just 26 seconds, a single exchange with "The Predator" costing Velasquez a knee and plenty of brain cells. It would prove to be the last time fans would see Cain step foot inside the Octagon.

To see the former champion dispatched so easily and suffer a major injury in the process was nothing short of depressing and brought about a sad end to Cain's historic career, one that had always felt incomplete thanks to his lengthy list of injury layoffs.

7. Chuck Liddell getting sparked out one last time (or so we thought)

When the "Iceman" made his final walk to the Octagon in Vancouver back in 2010, all indications were that the world would see a reinvigorated Chuck Liddell.

After his legendary title run ended with a second knockout loss to Rampage Jackson, Liddell's career trajectory had taken a nosedive. A close split decision loss to the unheralded Keith Jardine had many writing Liddell off completely, but a brilliant back-and-forth war with Wanderlei Silva breathed new life into Chuck's title aspirations.

And then Chuck ran into Rashad Evans. And Shogun Rua.

It was clear Liddell's once-iron chin simply wasn't what it used to be and after suffering three brutal knockouts in his last four outings, the calls for Liddell to retire became overwhelming. But Chuck wasn't having it.

Instead, Liddell would re-dedicate himself to the sport, getting into the best shape of his life to take on Tito Ortiz for a third time after the two coached against one another on the eleventh installment of The Ultimate Fighter.

Unfortunately, Ortiz would be forced to pull out of the trilogy fight due to injury and in stepped former middleweight champion Rich Franklin. Regardless of his opponent, Chuck was determined to prove his doubters wrong and show everyone that the Iceman still had what it takes.

When the Octagon door closed behind him at UFC 115, Liddell certainly lived up to his end of the bargain and gave the fans a show.

Not only was he in great shape, but he appeared to be a truly rejuvenated fighter - his combinations were sharp and powerful, his counters crisp, his long-forgotten kicks swift and deadly. Liddell had brought back his excellent kicking game that had for so long been absent from his appearances to great effect, even breaking Franklin's forearm with a kick in the opening round.

As the first round drew to a close, the MMA world rejoiced with the knowledge that the Iceman was back.

And then in the blink of an eye, he was gone.

With just seconds left in the round, Franklin appeared to be hurt from a Liddell salvo, enticing Chuck into pursuing the finish. Chuck "smelled blood", as they say. But in the heat of the moment, the Iceman got overzealous - forgetting entirely about defense, Liddell went in for the kill, running himself right onto a counter right hook from his wounded prey.

The shot sent Liddell crashing to the canvas, out cold at 4:55 of the first round.

It was a devastating and shocking finish that brought a tragic end to Chuck's UFC career.

While fans were certainly impressed by Franklin's toughness and slick counter KO, it was impossible not to feel bad for Chuck - he had put everything into turning his career around and for the better part of a round, he had looked better than ever, all for it to be undone in a single moment.

It was the legend's third straight clean knockout loss and the fourth in his last five outings; no matter how badly Liddell wanted it and no matter how good he looked on offense, his head simply couldn't take any more punishment. It was a bitter reminder that in MMA, none of your heroes are safe from the punishing clutches of age.

6. Mark Coleman getting trounced in front of his daughters

What happened at PRIDE 32 was the perfect example of why it isn't always a good idea for a fighter to bring their young children with them to watch them compete.

It may seem like a no brainer, but that hasn't stopped a handful of fighters over the years from doing just that.

It certainly makes for a great moment should that fighter win, but it can be downright heartbreaking if they lose in front of their kids - especially if they get brutally beat down in the process.

For the main event of the promotion's first trip to the United States, PRIDE paired up former UFC heavyweight champion Mark Coleman with their current champion Fedor Emilianenko.

The two had first met some 20 months prior in the 2004 Heavyweight Grand Prix, where Fedor had submitted the former Olympic wrestler in just over two minutes via armbar.

Since their first meeting, Coleman suffered a quick knockout loss at the hands of Mirko Cro Cop before putting together a two-fight winning streak with sub-minute wins in a squash match with Milco Voorn and then Shogun Rua, who broke his arm in a freak accident while bracing himself for a Coleman takedown.

Fedor on the other hand had continued his dominance over the heavyweight division, winning six straight in legendary bouts against the likes of Kevin Randleman, Antonio Rodrigo Nogueira, and Mirko Cro Cop in an epic "fight of the decade" (these wins were of course rounded out by a few typical PRIDE squash matches).

For their first trip stateside, PRIDE wanted a high-profile American to headline and Mark Coleman certainly fit the bill - despite his two-fight winning streak being rather unimpressive under a microscope, a win over Shogun regardless gave them ample justification to give Coleman a rematch with the heavyweight king in a non-title bout.

For his part, Coleman took the opportunity very seriously and did everything he could to try to win the fight - he just wasn't on Fedor's level.

Emilianenko battered the 41-year-old, turning Coleman's face into a swollen mess and nearly closing one of his eyes before securing another armbar victory in the second round.

Coleman had his moments and fought valiantly, but he was simply no match for the dominant Russian champion. It wouldn't have been a particularly memorable bout until the post-fight interviews however.

An emotional Coleman took the mic to tell his two young daughters, who sat ringside to witness their father getting smashed in the ring, that he loved them and that "daddy's okay".

Officials then brought the Coleman's kids into the ring to let them hug their father, the two girls bawling their eyes out in front of 12,000 people as Coleman kept telling them that he "feels great" and everything was okay.

He then brought them over to Fedor, the man who had just beat the holy hell out of their father, to show them that everything was okay. Fedor did his best to seem unimposing, and even let Coleman playfully "punch" him to try and lighten the mood, but despite their best efforts it did little to appease the upset little girls.

The entire post-fight sequence was hard to watch and remains to this day one of the most awkwardly depressing moments in MMA history.

5. Daniel Cormier coming up short against Jon Jones...again

If you've been an MMA fan for long, you're undoubtedly familiar with the rivalry between Daniel Cormier and Jon Jones.

Daniel Cormier entered the UFC in 2013 riding high off of his Strikeforce Heavyweight Grand Prix win, a title he had earned in full despite being an alternate in the tournament that gained entry due to Alistair Overeem's signing with the UFC.

He would quickly solidify himself as one of the top contenders in the heavyweight division upon his arrival in the UFC, but there was one problem - his best friend and teammate Cain Velasquez held the crown.

Being the great teammate and friend that Cormier is, "DC" opted to move down to the light heavyweight division, which was no small feat for the oddly built Olympian wrestler especially given that his hopes for a gold medal were dashed at the 2008 Olympic Games after he had suffered kidney failure while cutting weight.

The powerful wrestler managed to hit the mark and easily earned himself a shot at the title in his new weight class opposite Jon Jones - his polar opposite.

The two very different men immediately clashed and engaged in a heated war of words, tensions eventually boiling over at a press conference where the two fighters got into a scuffle on the stage and were fined and punished by the Nevada athletic commission as a result.

The intense rivalry resulted in a highly successful pay-per-view event, with Jones using his vast size advantage to great effect and shocking many by outwrestling the former captain for Team USA's Olympic wrestling program. Though the fight was closely contested, Jones took home an impressive decision victory and the rivalry settled down...for a moment.

Just a few months later Jon Jones would be stripped of his UFC title after causing a multi-car pileup which resulted in a broken arm for a pregnant woman in another vehicle, then fleeing the scene and likely avoiding a second DWI charge on his record. Cormier was then thrust right back into another championship fight against the next top contender, Anthony Johnson, whom he dominated en route to capturing the vacant light heavyweight title.

It would be quite some time (and plenty more controversy) before Jones and Cormier would meet for a second time inside the Octagon.

After defending his title in Jones' absense, a rematch was expected to take place early in 2016 before an injury sidelined Cormier until the summer - Jones opted to stay active and won a newly created interim light heavyweight title in the meantime, setting up a massive title unification bout against Cormier at the stacked UFC 200 card.

Just three days before their rematch, Jon Jones was flagged by USADA for estrogen blockers and subsequently pulled from the fight, with Cormier facing former middleweight king Anderson Silva in a non-title fight on just two days' notice to remain on the card.

Cormier would go on to once again dominate Anthony Johnson and defend his title while Jones served his doping suspension - in 2017, just over one year after their UFC 200 showdown fell through, Jones and Cormier finally met again at UFC 214.

Focusing much more on his striking rather than the wrestling-heavy attack he entered their first fight with, Cormier looked extremely sharp early, landing powerful combinations and heavy punches at will on Jones despite having a whopping 14" reach and 5" height disadvantage.

Though the first round was extremely close, Cormier looked to be pulling ahead in the second, his powerful and sharper hands giving him the edge in exchanges. Heading into the third round the fight was tied on the judges' scorecards, with Cormier holding all of the momentum.

And then DC's output fell off a cliff. Although he didn't appear to be fatigued (and his prior five round fights would also suggest this wasn't the problem) nor hurt, Cormier suddenly seemed content to just sit on the outside and walk toward Jones, parrying blows and looking to hand fight with the far longer fighter.

Jones happily made the most of the opportunity and proceeded to launch dozens of kicks from range at his foe's legs and body, racking up points as DC seemed to take the round off.

Cormier would later state that he got too comfortable and felt that nothing was hurting him - whatever caused it, it was a mistake that would cost him the title and his redemption against his most hated foe.

Jones launched a left high kick at Cormier; DC reached down to catch it, expecting another one of Jones' body kicks that he had been absorbing for much of the round, only for Jones' shin to smash into his face instead.

Wobbled badly, Cormier tried to retreat and fell as Jones attacked. Now pinned against the cage, DC was knocked out cold by vicious ground and pound that earned Jones back his undisputed light heavyweight title.

To see such a genuinely great figure in the sport get knocked out in vicious fashion by his bitter rival, after he had started off so well, was a hard pill to swallow. It was made much, much more difficult by Cormier's post-fight interview.

After being confused and extremely emotional following his first career knockout loss (something that does regularly happen to people following a knockout), a devastated Daniel Cormier was interviewed by Joe Rogan. Failing to hold back tears, the anguish Cormier was going through was as clear as day; he had been waiting for over two-and-a-half years for his chance at redemption, running through the best in the division all for a chance to prove that he was better than Jones.

Cormier (along with some fans) believed that, if he couldn't defeat Jon Jones, then he was never really the light heavyweight champion and was merely a placeholder. He had dedicated himself entirely to defeating Jones and put everything into the rematch - to come up short was nothing less than debilitating.

His response when Rogan asked him about where the rivalry would go from there particularly hit home - "if he wins both fights, there is no rivalry".

For his part, Jones acted surprisingly classy in victory and at least provided some sympathy for devastated fans rather than taking the opportunity to rub it in.

Of course, things would go back to normal as controversy once again found Jones when USADA flagged another of Jones' samples, this time from the day before their fight. Jones tested positive for the anabolic steroid turinobol and given it would be his second USADA violation, he was to be banned from competition for up to four years (he'd later have it reduced for informing on other cheaters).

Cormier's loss was overturned to a No Contest and he was subsequently reinstated as light heavyweight champion, later going on to capture the heavyweight crown and become the first concurrent two-division champion to defend both titles. To say that Cormier has experienced both the highest of highs in the sport, and the lowest of lows would be an understatement.

4. Jose Aldo's legendary title reign disappearing in 13 seconds

Sixteen wins. Nine knockouts. One WEC featherweight title. One UFC featherweight title. Nine title defenses.

Jose Aldo's legendary run spanning from his first career loss (in a bout up at lightweight) back in 2005 to his fight with Conor McGregor in 2015 saw "Scarface" absolutely dominate the 145-pound division for a decade.

Aldo burst onto the North American scene as a highly touted 10-1 prospect out of Brazil, the 22-year-old known to be an exceptional grappler with a Brazilian jiu-jitsu black belt under Andre Pederneiras.

He was immediately given a stiff test in the form of Alexandre Franca Nogueira, a former Shooto champion who was at one time regarded as one of the best featherweights on the planet.

Expecting to see the grappler show off his highly touted ground game, fans were shocked by Aldo's WEC debut thanks to his incredibly fast and powerful striking and his sublime takedown defense, the young prospect battering the experienced vet en route to a second round TKO victory.

From there, Aldo would cut through the entire division like a hot knife through butter, his explosive and technical striking baffling his opposition, his brutal leg kicks turning him into one of the most feared fighters on the planet, his brilliant ground game giving his victims no safe space when the cage door shut behind them.

Five straight knockouts followed (including an 8-second double knee over Cub Swanson), culminating in the destruction of Mike Brown which earned Aldo the WEC featherweight crown.

Aldo then headlined the WEC's first (and only) PPV event opposite former champion Urijah Faber in a fight that enthralled the MMA community, garnering a massive buyrate for a non-UFC event that inspired the UFC to absorb the WEC and its lighter weight classes into their ranks.

Aldo would absolutely dominate the California Kid for 25 gruelling minutes, completely destroying his legs with his devastating low kicks and turning his thigh into a swollen mess.

Another impressive knockout later, Aldo was promoted to a UFC champion as the WEC merged with its parent promotion and Jose dominantly defended his title in front of over 50,000 fans in Toronto at UFC 129, giving his opponent one of the biggest hematomas imaginable in the process.

Aldo would continue to dominate over the coming years, his aggression and ridiculous explosiveness reined in to keep his dominance on display over the course of five rounds, his brilliant defense stiffling his opponents at every turn while his destructive offense kept them fearing every exchange.

Wins over Kenny Florian, Chad Mendes, former lightweight champion Frankie Edgar, the Korean Zombie, and Ricardo Lamas followed, before perhaps the greatest fight in Aldo's career - a second meeting with Chad Mendes.

Mendes had put together a five-fight winning streak since their first meeting with four knockouts, running up his record to a stellar 16-1 and cementing his status as the second best featherweight on the planet. In addition to his dominant collegiate wrestling, Mendes' striking had improved in leaps and bounds, turning him one of the most powerful knockout artists in the division.

While his WEC career was riddled with knockouts, Aldo had drawn criticism for his overly conservative style more recently in the UFC, his vaunted offense increasingly geared less toward a finish and more on asserting his dominance in spurts as his sublime defense crippled his opponent's opportunities to score points or damage the featherweight king.

Against Mendes in their rematch however, Aldo was finally forced into higher gears and MMA fans were treated to one of the greatest fights in MMA history as a result.

Mendes drew (metaphorical) first blood in the rematch courtesy of a beautiful uppercut off of a faked takedown attempt which cracked Aldo - and only served to piss him off.

The fight was extremely competitive throughout, but it was Jose Aldo who shined brightest - his absolutely stellar takedown defense was on point throughout, with the NCAA Division I standout wrestler only able to secure a single takedown in the 25-minute war which scored nothing as Jose got back to his feet in a matter of moments.

His kickboxing, particularly his boxing, was simply on another level, his educated and diverse jab regularly keeping Mendes at bay, brilliant combinations rocking the contender on multiple occasions, sharp counters punishing his rival at every turn.

Aldo's somewhat questionable gas tank appeared to be on display as his output waned in the fourth round, the lone stanza that his challenger would pick up on the judges scorecards simply because his output was far higher - only for Aldo to come roaring back in the fifth, putting a stamp on his victory and ending the war in style.

It was a showcase of the two best featherweight fighters on the planet in 2014, but another featherweight contender waited in the wings - one Conor McGregor.

The rising Irish superstar had already been calling the champion out for some time as he climbed up the rankings, securing knockout after knockout to earn a title shot in July 2015 (albeit he had only fought one top ten fighter).

McGregor relentlessly harassed the Brazilian champion leading up to their massive encounter at UFC 189, but just two weeks before their meeting, Jose Aldo suffered a broken rib and was forced out of the main event. In stepped Chad Mendes, who despite being out on a hunting trip while next top contender Frankie Edgar was in a fight camp, was chosen by the UFC to be Conor's opponent for the interim featherweight crown.

Mendes started out strong with a dominant first round, landing heavy punches throughout and securing takedowns at will against the slick striker. McGregor weathered the early storm, landing shots of his own and digging in numerous front kicks to Mendes' body to help sap Chad's limited cardio given his lack of a fight camp.

In the second, Mendes faded badly and found himself at the mercy of McGregor's long, powerful strikes, succumbing to a slick one-two late in the round. McGregor had now rightfully earned his shot at Aldo's throne and the stage was set for an epic title unification at the end of the year.

Given the impressive PPV numbers UFC 189 pulled off despite the late replacement, the UFC opted to promote the featherweight title fight with a world tour, flying out the two headliners to various pressers as McGregor relentlessly antogonized the champion.

McGregor's antics were more than enough to get under anyone's skin, from putting his hands on Aldo when he was seated for an interview to stating that he was going to ride through the favelas in Brazil and slaughter his people; the champion was pissed off and rightfully so.

And that would ultimately prove to be his undoing.

The two finally met inside the cage at UFC 194 in one of the most highly anticipated showdowns in UFC history. It promised to be a war between the two best strikers in the division - only it wasn't to be.

The opening seconds started with McGregor throwing out a few feelers as Aldo looked for his opportunity to strike - and then it happened.

Just moments into the fight, Aldo opted to charge forward at the Irish counter striker, keeping his head on the centre line and looking for a lunging left hook. McGregor pounced, the title presented to him on a silver platter.

A left hand came barreling down the middle and landed flush on the champion's chin, Aldo's own momentum adding to its impact. A few hammer fists followed before the ref was able to step in, but they were unneccessary - the champion had already been knocked out cold by the first punch landed.

A single moment of over-aggression had costed Jose Aldo everything; his title, his pride, his decade-long winning streak.

On the biggest stage of his career, headlining a massive pay-per-view and finally getting his much-deserved time in the spotlight, Aldo fell in just 13 seconds.

Three thousand, six hundred, sixty eight days.

That's how long it had been since Aldo had last tasted defeat over a decade ago. And now here he was, laying on the canvas just moments after having been introduced to the crowd by Bruce Buffer, wondering where it all went wrong.

The loss was absolutely devastating for Aldo, the shocking and swift finish only made worse that it was at the hands of his most bitter rival, a man who had spent the last year relentlessly taunting and harassing the respectful and reserved champion. The worst part of the loss, as he would state in the post-fight interview, was that the fight had only just started - a single mistake right at the start and it was all over.

Even McGregor, who to his credit was very respectful following the victory (at least that night), stated that a champion like Aldo deserved a longer fight.

The UFC would then show footage from inside Aldo's locker room in the arena, the champion sobbing with his head in his hands as his corner joined him in misery.

One couldn't help but feel happy for McGregor, who despite his controversial antics, did seem to be a decent person deep down and had accomplished the unthinkable. But for Aldo, it was the single worst outcome imaginable and tore down one of the greatest legends in the sport in a matter of seconds, a single mistake costing him a decade of dominance and a chance to turn into the superstar a fighter of his caliber should have been all along.

Aldo would never get a chance to redeem himself in a rematch; McGregor would never compete again in the featherweight division, opting to move up to lightweight and even welterweight instead. The once-dominant champion would see mixed success in the years since, recapturing his featherweight crown by turning in an absolute masterclass against Frankie Edgar before losing back-to-back bouts with Max Holloway.

Though Aldo would see pockets of success in the aftermath and is still clearly one of the best fighters on the planet despite his noticeable decline, his loss to McGregor marked the end of the Aldo era and the legend has gone just 3-5 in the years since.

3. The ghost of BJ Penn being mauled by Frankie Edgar

BJ Penn could easily have multiple entries on this list (check out the honourable mentions), but easily the saddest fight of his career was his needless trilogy capper with Frankie Edgar.

In the early stages of 2010, BJ Penn was at the height of his powers - having stopped longtime contenders Kenny Florian and Diego Sanchez in the championship rounds of both of his prior title defenses, and having gone unbeaten at his natural weight class of lightweight since 2002, Penn was regarded as the greatest lightweight in MMA history and one of the greatest fighters to ever compete in the young sport.

For his fourth lightweight title defense, Penn was expected to make light work of the undersized wrestle-boxer Frankie Edgar.

In the UFC's first trip to Abu Dhabi back in 2010, their lightweight title tilt was surprisingly competitive - Edgar's constant movement and savvy footwork kept him from taking much punishment, while Penn's sharp boxing and impeccable takedown defense had him in control through most of the action.

Although much closer and more tepid than anticipated, fans were content that Penn had picked up another title defense with the vast majority of viewers scoring it 48-47 in his favour (three rounds to two). The judges however were watching a different fight, as all three awarded Edgar the decision and thus Penn's legendary title run came to an unceremonious and anticlimactic end.

The highly controversial decision forced an immediate rematch to be booked just four months later at UFC 118. Expected to right the perceived wrong he suffered at UFC 112, Penn was once again the favourite - this time however, there would be no controversy.

From the opening bell Edgar took charge, lancing Penn repeatedly with crisp combinations and getting out of dodge before Penn could return with any counters. Shockingly, Edgar even took down BJ, who was renowned for his sublime takedown defense even against much larger opponents.

A rather lethargic-looking Penn seemed asleep at the wheel, content to sit back and lose points while the hungry young Jersey boy went to work. There was no doubt the judges had the correct winner this time around with Penn failing to secure a single round on anyone's scorecards. A broken BJ Penn was left picking up the pieces to figure out what went wrong.

Edgar would go on to defend his title in the second and third fights of an epic trilogy against his rival Gray Maynard before losing the title in the same manner in which he won it - via a controversial decision.

After another immediate rematch saw the same (and once again controversial) result, Edgar dropped down to his more natural weight class of featherweight to challenge longtime kingpin Jose Aldo for his title, losing a decision to the Brazilian legend.

A dominant win over prospect Charles Oliveira however saw Edgar finally get back in the win column after a series of tough, extremely close decisions in championship fights.

Penn on the other hand saw his career continue to head in the wrong direction.

Following the losses to Edgar, Penn would move back up to welterweight and saw brief success with a blistering 21-second knockout of his old rival Matt Hughes to cap off their epic trilogy - that would prove to be the last win in Penn's storied career.

He would next compete against Jon Fitch, dominating the larger wrestler early before gassing out and getting demolished in the third round, hanging on to see the final bell before a draw was declared.

Similarly, Penn started off strong against Nick Diaz, only to gas out even earlier and get absolutely destroyed by a torrential onslaught of combinations from the lanky Stocktonian. His incredible toughness saw him survive once again to see the final bell, but after such a one-sided drubbing Penn decided to retire in the cage for the first time in what would be a recurring theme in the later stages of the Hawaiian's career.

A year later he would return from his "retirement", again at welterweight against the much larger Rory MacDonald. MacDonald easily beat on the aging vet (who was only 34 at the time) en route to a lopsided decision. Once again Penn would retire, but just over a year later the itch to compete would once again see Penn back in the Octagon.

Penn persuaded the UFC into giving him "one last chance" to avenge his losses to Frankie Edgar, this time at Edgar's new home of featherweight. Always a fighter that disliked weight cutting and instead liked to move up and take on larger opponents, Penn promised a rejuvenated fighter as he got himself in shape to make the cut to featherweight for the first time in his career.

The two would coach opposite one another in the 19th installment of The Ultimate Fighter, a season which saw the two rivals show nothing but respect for one another and reaffirm their position as two of the most well-liked figures in the sport.

Their third meeting was not well-received however - it was clear that Penn was a shell of his former self and his recent outings had seen the Hawaiian legend battered to a pulp only to enter short-lived "retirements" immediately after.

Edgar meanwhile was still clearly a top-shelf contender and considering it was also Penn's first attempt at making the featherweight limit, all signs pointed to the fight going like their last meeting and Edgar dominating.

No one quite foresaw just how bad their third fight would be however.

Though he looked in good shape, the once unstoppable BJ Penn that showed up to the Octagon in July 2014 was nothing short of a ghost under the ring lights.

Trying out a bizarre new stance for some inexplicable reason, the once-great boxer looked like an absolute amateur as he hopped around the cage in puzzling fashion, generating zero power on his punches and presenting an easy target for everything Edgar threw.

When Penn was easily taken down out of his disturbing new stance, he had a new "guard" waiting for Edgar - like his new look on the feet, Penn's movements on the ground were utterly bizarre and while his training partners and coaches insisted he was beating world class fighters in the gym with these new techniques, they did not work whatsoever against Frankie Edgar and made him look utterly incompetent.

After initially hesitating thanks to Penn's odd tactics, Edgar eventually engaged Penn on the mat as well, easily slicing through Penn's defenses (or lack thereof) and mauling the Hawaiian at every turn.

While Penn's ridiculous toughness was still fully in tact and kept him conscious, Penn took a horrific beating before the ref eventually saved him from any further punishment thanks to Edgar's unanswered onslaught of ground and pound late in the third round.

Not only was it a one-sided beating, but Penn completely embarassed himself in a way fans were simply not prepared for nor ever expected from someone as talented as BJ Penn.

It was a sad and brutal end to a legend's career that showed fans around the world just how depressing it can be to see a legend who doesn't know when to call it quits continue competing. Simply put, the UFC never should have put the third fight between the two together.

Except it unfortunately wasn't the end of his career.

Penn would seemingly retire for good following the embarassing beatdown, only to resurface two-and-a-half years later to lose another four straight bouts, breaking the UFC record for consecutive losses with seven in a row. He was then knocked out by an overweight civilian outside of a bar which finally forced the UFC to cut the disgraced legend, who had also found himself in trouble over domestic abuse allegations and other legal troubles.

Penn's late career has not only greatly tarnished his once sterling name, but it has caused an entire generation of fans to know a legend of the sport as nothing other than a glorified punching bag and as a result is one of the saddest stories in mixed martial arts' history.

2. Anderson Silva's traumatic attempt to reclaim his throne

By the time 2013 rolled around, Anderson Silva was on top of the world: the middleweight king had defended his crown a (then) record ten times, he had won a whopping seventeen straight fights with fifteen finishes, and had established himself as a major pay-per-view draw, something that had eluded the longtime champion earlier in his career.

Silva had appeared to be as dominant as ever at 38 years of age - after emphatically ending his epic rivalry with Chael Sonnen via a second round finish in their rematch, Anderson then went for another trip up to light heavyweight to take on Stephan Bonnar on extremely short notice to save a pay-per-view card ravaged by injuries.

Silva absolutely embarassed the UFC staple in a ridiculous display of bravado and skill, purposely standing against the cage and inviting Bonnar to hit him while he effortlessly avoided Bonnar's strikes or rolled with them to render them harmless. He toyed with Bonnar for the better part of five minutes before deciding his victim had endured enough for the night, handily finishing the tough vet with a vicious knee to the solar plexus.

The incredible show Silva put on once again reminded fans why Anderson Silva was widely considered the GOAT back then and how ridiculous his finishing abilities really were - and those abilities were indeed unparalleled. One need only look at his front kick knockout of Vitor Belfort, his dismantling of Forrest Griffin from inside of the matrix, his epic comeback submission victory over Chael Sonnen, his savage beatdowns of Rich Franklin or any of his other brilliant finishes over the years to see why Anderson Silva was a special breed of fighter.

His one perceived weakness over his reign had always been wrestling - fighters like Chael Sonnen, Travis Lutter, and even Dan Henderson all had success early in their bouts against Silva by grounding the striking savant and controlling him on the mat. A strong wrestler that also had excellent BJJ that would help them avoid being submitted was considered the ideal candidate to beat the middleweight champion, which brings us to Chris Weidman.

The undefeated 9-0 NCAA Division I All-American wrestler from New York brought not only his superb wrestling credentials to his highly anticipated matchup with Anderson, but also an impressive Brazilian jiu-jitsu game under the tutelage of Matt Serra, a large and powerful frame for the division, and even a measured and fundamentally sound striking arsenal to boot.

Riding high off of a vicious knockout of Mark Munoz, Weidman had convinced many that he was indeed the perfect blend of mixed martial artist to finally unseat the dominant champion, swaying betting lines to some of the closest odds for a Silva fight in years (Silva was still an almost 3-to-1 favourite).

Even though Silva would have the edge on the feet, many were confident in Weidman's ability to avoid taking too much punishment there and being able to ground Silva, where his impressive grappling capabilities and vicious ground and pound would give him a decided advantage.

Early on in their meeting at UFC 162, those thoughts were proven correct as Weidman was able to take Silva down early and dominate the Spider on the canvas.

Weidman easily secured the first round, but Silva was just getting started - after all, Silva lost the first rounds of virtually every fight he had against high-level wrestlers yet still managed to defeat them handily. And the end of the first round had also seen Silva begin to get loose, taunting his opponent while effortlessly avoiding his punches.

Sure enough, the second round started off with Silva firing off heavy leg kicks and continuing to tease his challenger, goading him into striking him. Many felt that Silva's taunting was unneccessary, but in reality, it was part of what made him so deadly - his gamesmanship was created to annoy and frustrate his opponents into abandoning their gameplans and becoming aggressive, at which point they would open themselves up to Silva's bread and butter - clean counter strikes.

Weidman came prepared however and kept his poise, refusing to overextend himself or chase his opponent and fall into the trap that so many other fighters had run into. Instead, he kept his technique tight with his feet firmly underneath himself; while Silva's games seemed to be keeping Weidman from shooting on him and turning it into a repeat of the first round, Silva needed Weidman to open himself up to present an opportunity for his counters and so his taunting quickly grew more and more bold.

Silva continued to show pure disdain for his opponent's striking capabilities and this tactic would soon prove disastrous.

After pretending to be hurt from a shot, Silva kept his hands in his pocket and rolled with Weidman's follow-up right hand, then continued extending himself backward at the waist to dodge a back-handed punch that proceeded the first. In doing so, Silva was now badly out of position; he had allowed Weidman to place himself firmly inside of Silva's stance and with Silva bent over backwards to avoid the first two strikes, he had nowhere left to move to avoid another strike.

A left hook caught Silva clean across the jaw as a result, sending him crashing unconscious to the canvas and shocking the entire world in the process. The knockout was as sudden as it was brutal, Anderson's head so far behind the rest of his body that he was simply in no position to be able to absorb any impact whatsoever.

The greatest title reign in the sport's history was over in a flash, the untouchable Silva's facade of invincibility reduced to rubble.

As clean as Weidman's finish may have been, many felt that Silva had defeated himself, his bad habit of "playing with his food" finally catching up to him as he underestimated his opponent or got too complacent after years of dominance. In all likelihood, it was a mixture of Silva's gamesmanship leading to an incredibly ill-advised decision and Chris Weidman's superbly prepared response to Silva's tactics. Weidman's discipline and the wise doubling up of his punches from both hands to force Silva into bad positions were what really secured him the victory, and without it he'd have ended up just like any of Silva's prior victims regardless of how much taunting Silva had done that night.

Given his legendary reign and the shocking manner in which the title changed hands, an immediate rematch was demanded by the MMA community and the two would meet again at the year-end card in December 2013.

The rematch quickly had fans realize that perhaps age had finally caught up to the former champion as not only did Chris Weidman once again dominate the first round, he even managed to drop Silva from inside his own famous muay thai plum.

The second round took place entirely on the feet just like in their first meeting, though with a much more serious Silva in the rematch. Anderson shifted his focus on landing leg kicks, the lone success he had in their first meeting, but Weidman had once again done his homework and repeatedly checked Silva's low kicks.

Rather than adjust his tactics, Silva instead doubled down on his leg assault, slamming another heavy leg kick into Weidman's knee as the champion checked it - hitting a knee of a shin with your own shin while throwing a leg kick is never fun, but what happened next was every fighter's nightmare.

Silva's shin split right in half on impact, his leg nearly wrapping around Weidman's as his limb flopped around as if made of rubber.

Anderson collapsed to the mat in utter agony and screamed in pain as he clutched his broken leg.

Not only had Silva once again lost and showed that he was human, but he was now the victim of the most grotesque injury in the sports' history.

As sad as it may have been to see Silva's reign come to such a shocking end in their first meeting, no one felt good about the result of their rematch. To see a legend screaming out in agony, writhing in pain as they carried him out of the Octagon on a stretcher, his leg shattered in what many at the time believed to be a career-ending injury - it was positively heartbreaking.

Though Silva would recover and return to the cage, the Spider's time at the top had come to an unceremonious end - after making a triumphant return against Nick Diaz the following year, Silva would tarnish his good name by testing positive for steroids and the legend would go just 1-4 (1 NC) in the years since.

1. A geriatric Chuck Liddell getting iced by Tito Ortiz

Chuck Liddell was the first real superstar in mixed martial arts and is one of the most revered figures in the sport. Alongside his (much more professional in nature) rivalry with Randy Couture, his feud with Tito Ortiz helped put the UFC on the map and brought the sport to new heights.

It all began in the early days of their careers - both men were managed by future UFC president Dana White at the time, and as a result Liddell was brought up to Big Bear to train with the reigning light heavyweight champion Ortiz. Legend has it that Chuck handed Tito an ass whooping in sparring and dropped him repeatedly with body shots, prompting Tito to avoid him like the plague from then on.

As Liddell continued racking up wins and Tito piled on title defenses, a fight between the two was inevitable (especially after Zuffa purchased the UFC and added Dana White as the promotion's president, thereby removing himself from managing either fighter) - but Tito had other plans.

Ortiz publically stated on multiple occasions that the two were close friends and that their friendship wasn't worth what they were being paid to fight - Liddell on the other hand claimed they had hung out and sparred together a few times but were far from friends, insisting that Ortiz was simply making up an excuse not to fight him.

The Iceman (and the UFC) grew increasingly resentful that Ortiz was essentially holding the title hostage and preventing him from getting his rightful shot at the UFC championship, a sentiment that the fans echoed.

Tensions continued to grow after Tito Ortiz smashed an aging Ken Shamrock and Liddell picked up his tenth straight victory; the UFC attempted to book the highly anticipated matchup in 2003 but Tito declined citing scheduling conflicts.

To force Tito's hand, the UFC created an interim light heavyweight title that would determine a mandatory challenger for Ortiz to face later that year, matching Liddell up with former heavyweight champion Randy Couture in his 205 pound debut.

While Couture was coming down from heavyweight, he was far from massive and was actually the size of most light heavyweights anyway, regularly weighing in under 220 pounds without cutting any weight. Combined with the fact that he was nearly 40 years old on fight night and had lost his last two fights, most expected Liddell to handle the aging Couture (as did the UFC) - unfortunately their plans were derailed as Couture shockingly dominated Liddell from pillar to post, TKOing him in the third round to capture the interim belt.

Later in 2003 Couture would go on to dominate Ortiz as well to unify the titles, making him the first man to capture UFC belts in multiple weight classes and wrecking the UFC's plans in the process.

Following Chuck's loss to Couture, Dana White chose to directly engage PRIDE FC, a Japanese MMA promotion and their largest competitor, by entering Chuck Liddell into PRIDE's 2003 Middleweight (equivalent to light heavyweight in the US) Grand Prix.

Still believing that Liddell was the best fighter in the world and would beat everyone that PRIDE could offer, White had intended to have his star face PRIDE's middleweight champion Wanderlei Silva but PRIDE had instead offered Liddell a spot in the tournament, the brackets working out so that the two could face each other in the finals should they both win their tournament matchups.

Confident in the Iceman's success, White bet big on Liddell and his quarter-final bout went according to plan when Liddell made quick work of highly touted prospect Alistair Overeem.

In the semi-finals however, Liddell found himself overpowered and at the mercy of a series of knees to the head while on the mat (perfectly legal in PRIDE) courtesy of Quinton "Rampage" Jackson en route to a second round corner stoppage.

With Ortiz coming off his title loss to Couture and Liddell coming off of losses in two of his last three, both men needed a big win to put themselves back into title contention.

Better late than never, Ortiz finally accepted a bout with Liddell and in 2004 the highly anticipated grudge match came to fruition, the bad blood between the two still whipping fans up into a frenzy despite their recent setbacks.

The two rivals spent most of the opening round at UFC 47 feeling each other out, with neither man landing much of significance or establishing dominance, but the tension was palpable; at the end of the round after Liddell landed several heavy shots, Tito taunted Chuck and pushed referee "Big" John McCarthy into him when he stepped in to signal the end of the round, continuing to hurl insults in the middle of the cage.

Early in the second round however, Liddell poured on the pressure and unloaded a vicious combo on a wounded Ortiz, dropping him to the canvas and stopping the former champion in emphatic fashion. Ortiz would later claim a thumb to the eye caused the stoppage and the bad blood between the two would continue to boil for more than two years before a rematch was finally signed.

Following his trouncing of Ortiz, the stage was set for a massive rematch between Liddell and Couture - to make the fight even bigger, the UFC opted to pit the two stars against one another as opposing coaches on the inaugural season of The Ultimate Fighter.

Not only was the show a massive success that created new stars for the UFC and ushered in a new era for the sport, but it helped hype up the light heavyweight championship rematch and propelled both men into mainstream stardom.

Come UFC 52, Liddell evened the score by knocking out Couture in just over two minutes to capture the ever-elusive title he coveted. The Iceman followed it up with a dominant shellacking of Jeremy Horn to avenge a prior loss, this time a submission that came in just the third fight of his career back in 1999.

A rubber match against Couture came in 2006 which saw Liddell put one of his famous rivalries (albeit not a hostile one) to bed for good with a second round knockout victory. For his third title defense, Liddell knocked out Renato "Babalu" Sobral in just 95 seconds.

Tito in the meantime also got back to his winning ways following the loss to Liddell; decision wins over Patrick Cote, Vitor Belfort, and Forrest Griffin preceeded a coaching gig of his own on The Ultimate Fighter's third season opposite Ken Shamrock. After a controversial stoppage, Tito would complete his trilogy with Shamrock in dominant fashion and pave the way for his shot at redemption against Liddell.

Following the explosion in the UFC's popularity thanks to The Ultimate Fighter and the two fighter's star power, the grudge match between Tito Ortiz and Chuck Liddell at UFC 66 was by far the biggest event the UFC had ever held. It sold some 1.1 million pay-per-views, by far the most in the company's history at the time and it managed to catch the attention of the entire sports world.

The rematch sported the same tension as the original but was accompanied by a more competitive and exciting fight - Liddell dropped Ortiz midway through the opening round but the challenger was able to survive and fight his way back into it, performing much better in the second where he landed solid shots of his own and was even able to take Liddell down momentarily.

In the third, both men landed hard shots but Liddell was relentless in his pursuit, clipping Ortiz with a left hand in one exchange that put the Huntingdon Beach Bad Boy on his back foot. A flurry of shots sent Ortiz to the canvas in an attempt to cover up, where Liddell would posture up and reign down punches until the ref eventually stepped in to save Ortiz from being pummelled any more while curled up in the fetal position.

The bad blood was settled and Chuck Liddell cemented his status as the baddest man on the planet with his fourth straight title defense, running his legendary knockout streak to seven in a row.

Tito was gracious in defeat and declared that Chuck was the greatest pound-for-pound fighter on the planet, finally burying the hatchet between the two in a nice display of sportsmanship.

Or so everyone thought.

No one knew it at the time, but their legendary bout at UFC 66 would mark the end of an era for both men as they entered the twilights of their respective careers.

Liddell would face Rampage Jackson for his fifth title defense, a rematch of Liddell's last loss back from his journey to PRIDE in an attempt to avenge the last of his career losses. Instead was knocked out cold in just under two minutes, his legendary title reign ground into dust.

A close split-decision loss to the unheralded Keith Jardine, who was a massive underdog going in, had many writing Liddell off as a shot fighter. Desperate to get back to his prior form, Liddell faced a similarly struggling Wanderlei Silva at the end of 2007 in a match fans had been wishing for for years.

The bout turned out to be the "last hurrah" for Liddell as the two wildly exchanged in a back-and-forth brawl for the ages that earned them Fight of the Year honours. It had many claiming that Liddell was back when he picked up the well-earned decision victory, and Chuck was once again in the mix for title contention.

Unfortunately for Chuck, his chin was no longer able to absorb the punishment it once was, and he was brutally knocked out in his next two fights in as many years, first by Rashad Evans and then by Mauricio Shogun Rua.

Ortiz on the other hand wasn't seeing himself getting knocked out, but injuries mounted and he simply couldn't manage to find a way to get his hand raised in the Octagon.

After his stinging loss to Liddell, Ortiz fought to a controversial draw against Rashad Evans before losing to future champion Lyoto Machida and dropping a close decision to Forrest Griffin, making him winless in his last four outings.

With both men in desperate need of a win but still holding drawing power and an intense dislike for one another, the UFC opted to pit them against each other as opposing coaches for the eleventh installment of The Ultimate Fighter.

Despite Liddell holding two wins over Tito, the fact that Liddell had been knocked out viciously in his last two outings and was in desperate need of a win, and that he didn't face as much risk of getting knocked out by someone like Ortiz, made the fight a viable option.

Had their trilogy bout taken place in 2010 as it was supposed to, their third fight certainly wouldn't find itself at the top of this list.

The two pulled in solid numbers each week and their mutual hatred was built into a big storyline once again, but as the show neared the end of taping, disaster struck. Ortiz suffered an injury and was forced to withdraw from their fight to undergo neck surgery, much to the chagrin of Liddell, who stated he knew Tito would back out of the fight and was never going to show up to fight him again.

Instead, former middleweight champion Rich Franklin, who was coming off of a knockout loss himself, stepped up to coach the remainder of the season and serve as Liddell's opponent in the Octagon upon the show's conclusion.

A rejuvenated Liddell looked spectacular early, landing heavy shots and even mixing in kicks nicely (one of which broke Franklin's forearm); with mere seconds to go in the opening round, Liddell's aggressive pursuit of a retreating Franklin cost him dearly as Rich landed a short right hand that sent the Iceman crashing to the canvas for the third straight time.

Although Liddell wanted to continue fighting, public pressure from his longtime friend and UFC president Dana White eventually got him to agree to retirement in exchange for a cushy executive gig with the UFC.

Ortiz would return later that year and lose a decision to Matt Hammill; going winless in his last five fights and still commanding a large paycheck, even a name as big as Tito's was on thin ice and in danger of being cut - the UFC offered him one last chance to keep his spot on the roster but pulled no punches as they pitted him against the heavy-hitting 12-1 prospect Ryan Bader.

Bader was a massive favourite going in and for good reason - not only were Bader's wrestling credentials superior to Tito's, he was a powerful knockout artist that would have a big advantage on the feet.

Or so everyone thought.

With his back against the wall, Tito shocked the world, dropping Bader with a short right hand and snatching up a tight guillotine to tap him out in under two minutes.

The massive upset seemingly breathed new life into Tito's UFC career, but that momentum was short-lived; just a month later Tito accepted a short-notice fight against Rashad Evans in a rematch of their draw some four years prior, where Tito was dominated and stopped via body shots in the second round.

He would finish his 2011 roller coaster ride with a crushing first round body shot TKO loss to Antonio Rogerio Nogueira, then lost a close decision to Forrest Griffin to complete their trilogy in 2012.

After sporting just one win in his last ten outings, Ortiz was finally let go by the UFC and entered retirement for a short period before signing to Bellator MMA.

There, he managed to find some success by beating a vastly undersized middleweight and grinding out a decision against the similarly aged Stephan Bonnar before being dominated by Bellator's light heavyweight champion.

It was clear Tito's time at the upper echelon of the division was done, but despite his decline he was still a good athlete and more than capable of competing with similarly past-their-prime fighters. He showed this in his last fight with Bellator in 2017 by defeating Chael Sonnen via a rear-naked choke in what he had announced would be his last MMA fight.

Money talks however, and so we finally get to the reason why this entry is on this list - the ill-fated trilogy bout between Tito Ortiz and Chuck Liddell.

After WME-IMG bought the UFC in 2016, Chuck Liddell's promised lifetime gig (where he really didn't do much of anything but cash cheques and attend fights) for the UFC was taken away as was his hefty salary.

Combined with the fact that Liddell had never wanted to retire in the first place and resented that he was forced to, the itch to compete and the chance to beat up Tito Ortiz once more became impossible for Liddell to refuse when Golden Boy Promotions proposed a third bout between the two.

Oscar De La Hoya, a renowned former champion in boxing and a prominent boxing promoter via his company Golden Boy, announced in 2018 that he would be entering into the MMA business. Promising a far greater share of revenue to the fighters, De La Hoya managed to sign Chuck Liddell and Tito Ortiz for the main event of his new promotion's inaugural event.

While the 48-year-old Liddell insisted he just wanted to compete (and indeed, had he gone to Bellator or another promotion he very well may have gotten a higher guaranteed figure), Ortiz claimed they were going to make millions and that he'd receive far more money with Golden Boy than he ever did fighting for the UFC. Spoiler alert: he didn't.

Regardless of reasons, fans weren't exactly thrilled to see Liddell, then 48, coming out of retirement - he had suffered several brutal knockout losses that led to his forced retirement and had lost his ability to take a shot some eight years prior, and that ability would only get worse with time.

Even a fighter not known for having much knockout power like Tito Ortiz was likely capable of knocking him out at the end of his career if he were to land a solid shot, but a Liddell eight years after that? It was pretty much guaranteed.

Chuck for his part certainly looked like he was in shape and was clearly taking his training very seriously, giving many fans hope that they'd get to see the Iceman of old one last time - nostalgia is a bitch - but concerns mounted as the fight grew closer.

First, John Hackleman, Liddell's longtime friend and head coach at The Pit (whose logo Liddell has tattooed on his arm and had coached him his entire career) refused to train Chuck at all for the fight.

Second, open workouts for the fight illustrated exactly why the matchup had drawn the ire of fans in the first place. While the 43-year-old Ortiz was no spring chicken himself, he was still athletic, strong and even though he could no longer compete with the upper echelon of the division, he could more than hold his own against lower competition and didn't look like he was stuck in molasses.

Liddell in the meantime looked like he was moving underwater when he hit the pads during his open workouts. Many fans witnessed the footage and genuinely thought Liddell was pulling a fast one on us, or "sandbagging" to use a boxing term - intentionally looking slow and out of shape to lull their opponent into a false sense of security. Even at 48 and after the punishment he put his body through (not to mention years of excessive partying), he surely couldn't be that slow and decrepit could he?

The answer was, unfortunately, yes.

Unlike some past legends (such as Randy Couture) that could compete at a high level even nearing their fifties, most fighters don't age very well and in the case of Chuck Liddell, the 48-year-old moved more like he was an 80-year-old man getting up off the couch.

As the terrible idea of a fight got started, it seemed that even Tito thought Liddell was trying to lure him into a trap as he cautiously circled away and felt him out, refusing to attempt anything significant. After Chuck awkwardly shuffled around and threw several telegraphed shots that were painfully slow and devoid of power, it became clear that this wasn't an act - Liddell was just that far gone.

Rather than the tension and excitement that surrounded their original bouts, their third matchup instead instilled an intense feeling of dread in fans around the world as it unfolded, the fact increasingly becoming clear that they were about to see a beloved legend of the sport take even more brain damage for no reason and at the hands of Tito Ortiz no less.

Everyone's worst fears were soon realized as late in the first round Ortiz finally stopped staring at his food and landed a combination that put Liddell unconscious. Ortiz celebrated as if he had just won a world championship while the rest of the MMA world just shook their head in shame and felt sick to their stomachs.

The MMA community collectively scorned Oscar De La Hoya for putting the fight together in the first place, not to mention the commission that signed off on it despite Liddell's geriatric condition.

The fight put a final, sad seal on Liddell's historic career and tarnished the memory of what was one of the greatest rivalries in MMA history.

Possibly the saddest aspect of the entire fiasco was the fact that Liddell was so convinced that he still had it; in interviews he had stated that he still believed he could beat Jon Jones and others at the top of the sport despite his age, and that he felt better than he ever did. This wasn't just talk to promote a fight - Liddell genuinely believed what he was saying.

It's that unflinching self-belief and confidence that makes so many fighters great that also forces them to stay in the game far too long and suffer unneccessary damage because they can't quit doing what they love.

Unlike their prior two fights in the UFC, the third was a financial disaster (thankfully) and prompted Golden Boy to cancel their plans for mixed martial arts promotion, with Tito later admitting his final pay was nowhere near what he had hoped thanks to the event's failure (largely from De La Hoya's complete ignorance when it came to MMA).

The poorly managed event was truly a disaster in every sense of the word and this trilogy bout never should have been signed, let alone allowed to take place.

For his part Liddell stated after the fight that he had no regrets and wouldn't have been able to live with himself had he not tried, and was just happy that he had the opportunity to give it one last shot even if it didn't work out in his favour; Ortiz on the other hand looks to continue to make easy money by fighting washed up fighters or vastly inexperienced competition, as shown by his bout late last year against famous pro wrestler and extremely poor MMA fighter Alberto Del Rio.

The incredibly bad main event of Golden Boy's lone MMA card remains the saddest fight in MMA history and hopefully it's the last time a legend stays in the game years after they should have retired.

Oh who am I kidding, Shogun Rua and Lil Nog are fighting each other again this weekend...

Honourable Mentions:

Kelvin Gastelum's execution of Michael Bisping

Fedor Emilianenko getting mauled by Bigfoot Silva

Randy Couture getting crane kicked by Lyoto Machida

Lyoto Machida handing Vitor Belfort his second front kick KO loss

Kazushi Sakuraba being fed to Melvin Manhoef

Wanderlei Silva getting faceplanted by Chris Leben

Jon Jones' demolition of Shogun Rua

BJ Penn getting massacred by Yair Rodriguez, Nick Diaz and Rory MacDonald


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