Top 5 Trilogy Fights That Never Should Have Happened in MMA

Before the current coronavirus hysteria, trilogy bouts were fresh on the minds of boxing fans. Two big trilogies have already been confirmed (though when they occur is no longer set in stone) - Deontay Wilder's execution of his rematch clause shortly after the drubbing he suffered at the hands of Tyson Fury in February sets up a third bout between the two, and more recently a third bout between Canelo Alvarez and GGG has been confirmed as well.


The latter bout is very much needed as Canelo holds a 1-0-1 record against Gennady Golovkin despite Golovkin pretty convincingly winning both bouts in the minds of most. Canelo and his management have taken a Mayweather-esque approach to both rematches with the older Golovkin, delaying the fights that fans want to see for extensive periods in the hopes that the Kazakhstani bomber slows down and thus poses less risk to Oscar de la Hoya's money maker.


It's a situation that makes a strong case for including rematch clauses in boxing contracts; on the complete opposite end of the spectrum, we have a rematch clause being used to force a third bout in near future that isn't justified and actively makes a strong case against rematch clauses.


Their first heavyweight title tilt was a tense and incredibly memorable affair - the brash Englishman danced around and used his awkward style to bank points against his sloppy opponent, but Wilder's fight-changing power resulted in two knockdowns - the second of which was the stuff of legends. Despite being knocked seemingly out cold, Fury rose from the dead like the Undertaker of WWE fame to narrowly beat the referee's count and somehow remain in the fight.


From there, Fury won the rest of the round and continued to outwork Wilder, to what most believed would be a hard-fought decision victory. Instead, the referees declared the bout a draw - following some promoter shenanigans, the two finally stepped into the ring once again over a year after their first meeting, their rematch a massive show drawing the attention of fight fans the world over.


Fury righted the wrong of the first match and thoroughly embarassed the "Bronze Bomber", finishing him in the 7th after Wilder's corner mercifully threw in the towel. Deontay was thoroughly outclassed and showed nothing in the fight that warrants him an immediate rematch - his pitiful excuses after the loss haven't exactly convinced anyone he has a chance of turning things around anytime soon, but thanks to the rematch clause in their bout agreement an immediate rematch has been confirmed.


The third fight will no doubt still make money, but it's hardly the fight fans are clamouring for - sporting-wise, it also does a disservice to Wilder as he will have less time to make required adjustments to his game where a tune-up fight or step back in competition would give him a much better shot in any future rematch, but the sizable payday he'll receive outweighs those concerns of course.


Just like in boxing, MMA has had its fair share of trilogies and many have proven to not only contain great fights, but have helped build the sport into what it is today. Liddell-Couture, Penn-Hughes, Velasquez-Dos Santos, Edgar-Maynard all spring to mind just to name a few, and a massive rubber match between Stipe Miocic and Daniel Cormier for the heavyweight title is also currently in the works (should it survive the coronapocalypse).


While MMA doesn't have to deal with rematch clauses, promoters have still put on their fair share of odd and downright perplexing rematches and trilogy bouts. No, I'm not talking about a third meeting between two relevant fighters that ended up being a dud, but rather trilogy matches that made little sense before the two fighters locked horns for a third time.


Longtime fans will likely think of the famously bad third meeting between Tim Sylvia and Andrei Arlovski as an example of a bad trilogy booking because of how the fight turned out, but in truth it was never a bad fight on paper.


At the time, Tim Sylvia and Andrei Arlovski were cutting through the rest of the division and were 1-1 against each other, with each man touting a quick first round finish over the other - there was never any indication beforehand that a rubber match between the two would end up being one of the most painfully boring title fights in UFC history, and thus it was not a bad booking.


This list instead looks at trilogy bouts that never should have been booked in the first place and made little-to-no sense competitively - whether their prior meetings be one-sided drubbings or their final bout made so many years after relevancy it became a sad affair, these are trilogy cappers that never should have been signed to begin with.


5. Charles Oliveira vs. Nik Lentz III

Just to be clear, the #5 spot on this list will be going to Shogun Rua and Antonio Rogerio Nogueira's third bout should the two fight in May (or later), but given Lil Nog's history of pulling out of events with injuries and the current state of business, who knows if the two legends will ever actually make it to the Octagon for a third meeting.


So until that bout between vastly past-their-prime PRIDE stars happens, Charles Oliveira's trio of bouts with Nik Lentz has secured the fifth place spot.


Their trilogy at least gets some points for having entertaining fights and finishes (including in their trilogy finale, even if it was one-sided), but it earns its place on this list for the bizarre booking of said finale.


When the two lightweight prospects first met in 2011, Nik Lentz had racked up an impressive 21-3-2 record with five wins and one draw in his six UFC bouts; the 21-year-old Charles Oliveira meanwhile was coming off his very first loss after starting his career a perfect 14-0 with all but one of his fights ending before the final bell, including his two prior UFC wins.


Lentz was seen as a tough test for the young Brazilian submission artist as he had a strong wrestling background and was known for being a grinder and wearing on his opponents. Their meeting ended up being a dogfight with the Brazilian getting the better of most exchanges; in the second round, after hitting Lentz with an illegal knee on the ground Oliveira secured a rear-naked choke submission for the win.


Or so he thought - due to the illegal strike which led to the finishing sequence, Oliveira's win was later deemed a No Contest. Although an immediate rematch would have been fair, given how the fight was going there was little interest in holding up Oliveira in what most fans saw as a win regardless.


Three years later the two would be booked for a rematch down at featherweight (both men had dropped down to the lower weight class in the years following their first meeting) only for Oliveira to miss weight and subsequently be pulled from the fight after falling ill.


In 2015 the two would finally meet again - the young Brazilian was riding a 3-fight win streak at the time and had gone 5-3 since 2011, while Lentz had similarly gone 4-3 in that time span. The now-featherweights would put on another Fight of the Night scrap, with Oliveira once again picking up a submission, this time in the third round via a guillotine choke that also earned him a performance bonus (and came without controversy).


In the years after Lentz would solidify his place as a dependable mid-card grinder, returning to lightweight and going 5-2 against opponents of varying caliber. Oliveira on the other hand saw his career take a downturn as he lost three of his next four bouts, being finished in each and missing the featherweight limit on two occassions.


Oliveira would be forced by the UFC to move back up to lightweight, where he would go 1-1 before improvements in his striking and poise saw him put together the best run of his career. Oliveira rattled off four straight submission victories which saw the Brazilian surpass Royce Gracie's record for submissions in the UFC (11) and run that record up to 13.


While Oliveira was on the doorstep of title contention and looking like a world-beater, Nik Lentz remained far lower in the pecking order and with (arguably) two losses already to Oliveira, it made very little sense for the UFC to book a third meeting between the two in 2019, but the UFC did so anyway.


If there was any doubt (there wasn't) as to who the better fighter was, Oliveira put those doubts to bed by skewering Lentz on the feet before stopping the durable wrestler with strikes in the second round.


The trilogy started off competitive and had a lot of excitement throughout, but the third bout was simply unneccessary and really did nothing for either fighter, earning it a spot on this list.


4. Wanderlei Silva vs. Kazushi Sakuraba III

MMA fans need no introduction to the two men involved in this trilogy - both are bonafide MMA royalty, with Kazushi Sakuraba being the biggest star from Japan to ever grace the sport and Wanderlei Silva being one of the biggest names in the sport's history.


At the time of their first meeting in 2001, both fighters were streaking through the PRIDE middleweight (the equivalent of light heavyweight outside of Japan) ranks.


The 12-2-1 Sakuraba was riding high on a three-fight winning streak that included his legendary arm-breaking kimura on Renzo Gracie after his remarkable run in the PRIDE 2000 Openweight Grand Prix.


Wanderlei meanwhile was similarly on a three fight winning streak (ignoring a quick No Contest due to an accidental groin strike) which included an impressive decision win over Dan Henderson following his disappointing decision loss for the vacant UFC title at the hands of Tito Ortiz.


At PRIDE 13: Collision Course in 2001, the "Axe Murderer" made quick work of Sakuraba, stopping him with a barrage of knees and soccer kicks in just 98 seconds.


It wasn't exactly the war fans were expecting, but it further solidifed Wanderlei's aura of lethality at the time that would only grow during his legendary unbeaten run that lasted until late in 2004 and spanned some 17 fights.


Sakuraba went on to defeat promising prospect and future star Quinton Rampage Jackson via first round submission in Jackson's PRIDE debut.


On the other side of the bracket PRIDE threw Wanderlei a soft ball in the form of a 1-1 opponent who was squashed in just 30 seconds before the rematch with Sakuraba was signed, this time for the inaugural PRIDE middleweight (equivalent to light heavyweight in the US) title just eight months after their first meeting.


Wanderlei would once again beat on Sakuraba, though this time the Japanese legend hung on and got some shots of his own in; after a tough 10-minute opening round, Wanderlei Silva was awarded the victory via doctor's stoppage due to Sakuraba's broken clavicle. It may have been an anticlimactic finish, but the end result was never really in question - Sakuraba just didn't have an answer for Wanderlei's vicious style.


Following their pair of bouts in 2001, Wanderlei would go unbeaten in five straight, knocking out four of his victims and battering Mirko Cro Cop in a special rules bout (as it was fought under special rules and neither man was knocked out, it was ruled a draw as no judges were assigned).


Sakuraba on the other hand went 1-2 during the same period, getting finished in both of his losses (one of which was to the afforementioned Mirko Cro Cop) with his lone win coming against a vastly overmatched opponent in just his second professional bout.


Fans weren't exactly eager to see Sakuraba get demolished in a third matchup against the Axe Murderer, but in the opening round of the PRIDE 2003 Middleweight Grand Prix, that's what they received regardless.


With Wanderlei already having won twice against Sakuraba and having established himself as one of the most feared fighters on the planet while Sakuraba's best years were already in the rear-view mirror, there really was no reason to make a third bout between the two men from a competitive standpoint. It was always going to be a sad and ugly affair, seeing a legend get knocked out once again in a fight he didn't belong in.


And that's exactly what it was - countering off a leg kick, Wanderlei hit Sakuraba with a stiff one-two that sent Sakuraba tumbling to the canvas as stiff as a board in the opening round.


It may have added another knockout to Wanderlei's legendary highlight reel, but it was a highly unneccessary and depressing finale to a one-sided trilogy that never should have happened.


3. Tito Ortiz vs. Ken Shamrock III

There's no doubt that the rivalry between Tito Ortiz and Ken Shamrock was massive for the UFC back in the old days, and is still regarded as one of the best rivalries and trilogies in the sport's history. It has a long and complicated story that spanned many years and was a monumental feud that was essential to the UFC's survival at the time.


That doesn't change the fact that their trilogy was a one-sided affair that shouldn't have gotten a third bout.


The rivalry started all the way back in 1997 at UFC 13, the night that Tito Ortiz's MMA career began.


After successfully making his MMA debut with a 31-second TKO finish in an alternate bout for UFC 13's light heavyweight tournament, Ortiz filled in as an injury replacement for the tournament's final opposite Guy Mezger, a prominent member of Ken Shamrock's fight team dubbed the "Lion's Den".


Tito saw early success against his much more experienced foe before falling into a guillotine and tapping out just three minutes into the bout.


After picking up a win outside of the UFC, Ortiz would return and upset Jerry Bohlander, another member of the Lion's Den - following the bout, Ortiz drew the ire of the Lion's Den founder when he pretended that he was shooting at Bohlander's corner after his win and then put on a T-shirt that said "I just f**ked your ass".


Tito went on to dominate a rematch with Guy Mezger, avenging his only career loss in emphatic fashion - it's what he did after the fight that ignited a war between him and the first fight team in MMA's history.


In what would surely go viral (and probably get him fined for "homophobia") in today's society, after earning a stoppage win against Mezger, Ortiz immediately fingered Mezger's corner and then threw on a T-shirt that said "Gay Mezger is my Bitch".


Fuming, Shamrock hopped up onto the cage as the Octagon turned into chaos and officials stepped in to prevent a melee in the cage (including "Big" John McCarthy, who literally picked up Ortiz like a child and moved him away from Mezger's corner in hilarious fashion).


At the time, Shamrock was one of the most feared and respected individuals in the sport and because he weighed around 240 pounds and competed up at heavyweight, most thought the "World's Most Dangerous Man" was simply too big for Ortiz - his adopted brother Frank however, was the current champion in Tito's own weight class.


Marketed as a grudge match given Tito's history with Ken and the Lion's Den, the reality is a bit less exciting - Frank had left the Lion's Den under bad terms over a year prior and had a falling out with his brother, and thus really wasn't involved in nor did he care for the feud.


The performance against Mezger earned Tito a title shot against Frank Shamrock regardless at UFC 22 in 1999.


Ortiz did well throughout the bout, controlling the longtime champion and imposing his fearsome top game on the well-rounded Shamrock in a great scrap that earned them the "Fight of the Year" back in the early days of MMA publications. It all fell apart in the fourth round for Tito however, as Shamrock fought his way back and rocked the "Huntingdon Beach Bad Boy" en route to a submission stoppage due to strikes.


Following his record (at the time) fourth successful title defense against Tito, Frank retired from the sport, vacating his title in the process. Facing fellow top contender Wanderlei Silva, Tito Ortiz captured the vacant belt shortly after with a clear decision victory in his second shot at gold.


Ortiz went on to defend his title four times, three of those coming via stoppage (including a vicious slam KO over Evan Tanner).


On the other hand, Ken Shamrock was experiencing mixed results in his own career.


Leaving the sport to focus on pro wrestling after last competing in late 1996, Shamrock had left the sport with an impressive 23-5-2 record and a reputation as one of the most fearsome fighters on the planet.


He would return to the sport in 2000 to compete in PRIDE, posting just a 1-2 record with the promotion (he also picked up a win in a smaller organization in the US, making him 2-2 overall during that time span). He had also slimmed down and was competing at around 220 pounds, making a cut to light heavyweight a no-brainer.


Despite his lackluster recent results, Ken Shamrock was still one of the biggest names in the sport and thus it was a big deal when the UFC managed to re-sign him to the promotion in 2002, some six years since Ken had last competed with the company.


And who would welcome Shamrock back to the UFC?


None other than reigning UFC light heavyweight champion Tito Ortiz.


Set for UFC 40: Vendetta, Zuffa had themselves their first successful show in what many would later say provided the glimmer of hope that inspired the struggling organization to keep going despite mounting financial losses.


The grudge match ignited the MMA community and both men sold the feeling that they genuinely hated each other - the feud inspired mainstream media outlets such as ESPN and USA Today to cover the event and interview the two combatants, something that was unheard of at the time in the sport.


Their trash talking was often hilarious (though not intentionally) - no MMA fan can ever forget the pre-fight press conference where Ken took the podium and promised to beat Tito "into the living death" while trying to look as intimidating as possible, only for Tito to burst into laughter prompting Shamrock to kick a chair into the air for Dana White to catch.


Their cringey pre-fight banter led to the UFC selling out the MGM Grand Garden Arena and selling some 150,000 pay-per-views, more than three times the buys UFCs were regularly garnering at the time.


The first real "big" UFC fight delivered from the start as Shamrock clipped Tito early and dropped the young champion to a knee - from then on however, it was all Tito. Repeatedly taking Ken down, Ortiz delivered his patented ground and pound, relentlessly hammering away on his rival while facing very little resistance from his aging rival.


Though most knew that Shamrock was past his prime heading into the bout (he was already 38 and had suffered extensive injuries over the years from both MMA and pro wrestling), his size and power coming down from heavyweight combined with his overall skillset had most unsure of what would happen when the two stepped into the cage.


In reality, the younger champion simply dominated the Lion's Den founder and after the third round, Shamrock's corner threw in the towel to save him from further punishment. With the win, Tito passed Frank's record for title defenses and set the new record for concurrent title defenses at five, seemingly settling his feud with Shamrock in the process.


But the feud was far from over.


Shamrock would explain that he had suffered a torn ACL prior to the Ortiz bout (which contributed to his lack of takedown defense) that would see him sidelined for nearly two years.


In the meantime, Ortiz lost his very next fight at the hands of the legendary Randy Couture after he had dropped down to light heavyweight, ending Ortiz's historic title reign. Following the loss of his title, Tito finally squared off in a grudge match with Chuck Liddell after years of buildup, a fight that saw Tito Ortiz knocked out in the second round.


Upon his return, Ken Shamrock took on early UFC competitor Kimo Leopoldo back up at heavyweight and knocked him out in under 90 seconds; despite his time off and having suffered a loss to Ortiz, Shamrock's star power was as strong as ever as his bout with Leopoldo drew more buys than the highly anticipated grudge match between Ortiz and Liddell just two months prior.


Ortiz would get back to his winning ways shortly enough, beating a late replacement in Patrick Cote and following it up with a close split decision victory over Vitor Belfort.


For Shamrock's next bout, he would take on rising talent Rich Franklin in the main event of the very first UFC event ever broadcast live on cable TV - the finale for the inaugural season of The Ultimate Fighter.


Shamrock claimed that he originally signed on to fight Tito Ortiz in a rematch on the historic card, but was instead given Franklin after Ortiz refused the fight. Shamrock was knocked out in under three minutes and Rich Franklin became a new star for the UFC, capturing the UFC crown down at middleweight shortly after.


Shamrock would continue harrassing Dana White for a rematch with Ortiz, with Ortiz allegedly turning down the bout on several occasions. Shamrock then went overseas to compete once again in PRIDE, where he would be knocked out for the second time in as many fights, this time against a much smaller but no less renowned fighter in Kazushi Sakuraba.


Despite coming off of two straight losses, Shamrock was finally granted his rematch with Ortiz as the UFC announced that Tito had finally accepted the bout and the two rivals would serve as opposing coaches for the third season of their hit show, The Ultimate Fighter.


Oddly, Ortiz chose to keep busy and actually fought the original TUF winner Forrest Griffin in April of 2006, just over a week after the first episode of his season of The Ultimate Fighter aired - Ortiz won a close split decision to improve his winning streak to three heading into his rematch with Shamrock.


At the conclusion of their incredibly heated season of TUF, Ortiz finally met Shamrock once again inside the Octagon. Unlike their first "pick-em" fight, Ortiz was a heavy favourite given Shamrock's age (now 42) and his clear decline in performance, especially considering he had been knocked out in his last two outings.


Regardless their massive rematch at UFC 61 set new records for the UFC at the time, drawing around 775,000 PPV buys and an impressive $3.4 million gate. Unfortunately, unlike their first bout it didn't live up to the hype; after Shamrock came out firing off combinations, Ortiz quickly secured a takedown and began hammering his rival with elbows from the guard, causing the washed up vet to go limp momentarily.


Referee Herb Dean called the bout just 78 seconds into the action, much to the chagrin of Shamrock and all of the fans in attendance. While it was a bit of an early stoppage, Shamrock really had no business being in the cage in the first place and was well on his way to being stopped regardless of the early intervention, and did in fact go limp for a moment before being resuscitated by another strike. Whether the stoppage was warranted or not, a third bout between the two was immediately announced anyway to resolve the feud once and for all.


Rather than put it on PPV which likely would have been very lucrative just like the last fight, the UFC opted to put the trilogy bout on Spike TV for free; it proved to be a savvy business decision as over 5.7 million viewers tuned in to their main event bout which in turn led to a rash of more mainstream advertisers being lured into the UFC fold.


Unfortunately for Shamrock, his final shot at redemption was not even remotely competitive and saw Ortiz finish the UFC legend in less than two-and-a-half minutes via strikes, this time without any controversy over the stoppage.


Ortiz gloated with his patented "grave digger" celebration before flipping him the finger and putting on a shirt that read "Punishing Him into Retirement".


Shamrock however approached Ortiz and buried the hatchet, saying it was just business and offering his hand which Ortiz accepted. Ortiz showed surprising maturity and stated that Shamrock had made him a better fighter and that he had always looked up to the legend, thanking him for "passing the torch".


It was a feel-good moment to see the two rivals finally end their feud, even if seeing an old man far past his prime helplessly beat up had left a sour taste in your mouth just moments earlier.


Shamrock would partially retire before coming back to much smaller shows in 2008, going 2-3 against weak opposition before officially retiring in 2010...only to come back in 2015 to fight for Bellator at the age of 52. He would be knocked out by Kimbo Slice before getting finished by strikes from Royce Gracie of all people a year later and then finally calling it a career (or so we hope).


The trilogy was essential to the growth of the sport and as such wasn't a bad booking in business or historical terms, but in terms of competitiveness it really shouldn't have seen a second fight much less a third one, controversial stoppage or not.


2. Frankie Edgar vs. BJ Penn III

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 who sported an impressive 12-1 record.


At the massive UFC 112 event in Abu Dhabi, 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 his fourth title defense with a likely score of 48-47 (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. Shockingly, Edgar even took down Penn, who was renowned for his sublime takedown defense.


A rather lethargic-looking Penn seemed asleep at the wheel, content to sit back and lose points while the hungry young champion went to work. There was no doubt the judges had the correct winner this time around, and 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 immediate 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 historic 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 rare 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 of Penn's late career.


A year later he would return to action, 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 opted to come back to face Frankie Edgar in an attempt to avenge his prior losses, this time deciding to cut weight and drop down to featherweight for the first time in his career to follow Edgar to his new home at 145 pounds.


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-flight 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.


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 unknown reason, the once-great boxer looked like an absolute amateur as he hopped around the cage in puzzling fashion, generating zero power on his once-lauded punches and presenting an easy target for everything Edgar threw.


When Penn was easily taken down out of his bizarre new stance, he had a new "guard" waiting for Edgar - like his new stance, 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.


After initially hesitating thanks to Penn's peculiar 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 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.


It was a sad and brutal bout 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.


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.


Despite this, the UFC was willing to give Penn one final chance before a drunken bar brawl saw Penn knocked out by an overweight civilian and finally forced the UFC to cut the disgraced legend, who had also found himself in trouble over domestic abuse allegations and other legal troubles.


1. Chuck Liddell vs. Tito Ortiz III

Love him or hate him, Tito Ortiz has been involved in some of the biggest and most important feuds in the sport's history, and nothing tops his rivalry with the "Iceman", Chuck Liddell.


It all began in the early days of their careers - both men were managed by future UFC president Dana White, and legend has it that Liddell was brought up to Big Bear to train with the reigning light heavyweight champion Ortiz. By both Liddell and White's accounts, Chuck handled Tito in sparring and dropped him with body shots, prompting Tito to avoid him like the plague from then on.


As Liddell continued racking up wins and Tito title defenses, a fight between the two was highly anticipated (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. Liddell grew increasingly resentful that Ortiz was essentially holding the title hostage and stopping him from getting his rightful shot at the UFC championship.


Tensions continued to grow as MMA fans increasingly clamoured for the fight to be made 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.


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.


Following Chuck's loss to Couture, Dana White chose to directly engage PRIDE FC, the 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 win their tournament matchups.


Confident in the Iceman's success, White bet big on Liddell and his quarter-final bout went according to plan as Liddell knocked out Alistair Overeem in just over three minutes.


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 see 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 shots, Tito then taunted Chuck and pushed referee "Big" John McCarthy into Liddell 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.


Earning his way back into title contention with the Ortiz knockout, a controversial cut stoppage forced an immediate rematch between Randy Couture and Vitor Belfort and put Liddell's shot at the crown on hold. While he waited, Liddell handily floored the overmatched 20-24-2 Vernon White to stay in fight shape.


With Couture reclaiming his title, 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 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 we 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. He was knocked out cold in just under two minutes, his legendary title reign smashed into pieces.


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 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, it wouldn't be an entry on 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 had stated he knew Tito would back out of the fight and would never make it to the cage 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) 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, considering a good payday was only there if the event was a success), 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, now 48, coming out of retirement - he had suffered brutal knockout losses that led to his retirement and had lost his ability to take a shot some eight years ago, and that ability would only get worse with time. Even a fighter not known for tremendous knockout power like Tito Ortiz was likely capable of knocking him out at the end of his career, 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, 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) refused to train Chuck 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.


Liddell in the meantime looked like he was 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 a resounding yes.


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. After Chuck awkwardly shuffled around and threw several big 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, knowing that we were going to see a legend take even more brain damage for no damn reason.


Everyone's worst fears were soon realized as late in the first round Ortiz finally stopped playing with 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 and felt sick to their stomach.


Fans scorned Oscar De La Hoya for putting the fight together in the first place, not to mention the commissions 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. It's that unflinching self-belief and confidence that makes so many fighters great that also forces them to stay 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 event 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 happy that he had the opportunity to do so even if it didn't work out; 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 poor MMA fighter Alberto Del Rio.


One would hope that the poor reception and financial failure that was Liddell vs. Ortiz III would be enough to deter promoters from putting on similar fights in the future, but if you follow combat sports, you know that it won't. Promotions (even larger ones, like Bellator in particular) still regularly showcase incredibly damaged and past-their-prime fighters and as long as people tune in, they will continue to do so.


(Dis)honourable mentions: Antonio Rodrigo Nogueira vs. Heath Herring III, Vitor Belfort vs. Dan Henderson III, Jeremy Horn vs. Chael Sonnen III

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