The massive fight between 19-0 middleweight champion Israel Adesanya and 13-0 top contender Paulo Costa is just days away and the MMA world is justifiably amped up for the tantilizing title fight.
It's just the second UFC men's title fight to pit two undefeated fighters against one another and although Israel Adesanya is coming off a career-low performance (or lack thereof) against Yoel Romero in his last middleweight title "defense", given Costa's unrelenting pressure and fearless aggression there is little chance that the fight isn't entertaining for as long as it lasts.
As I wrote those words however, I'm reminded of how excited I, like all MMA fans, was prior to Adesanya's last bout, which got me thinking about other disappointing fights in UFC history.
Rather than just picking the worst fights in UFC history, of which bouts between fighters with subpar skills would feature most prominently, instead this list deals with pure disappointment - these are fights that fans were extremely excited about that ended up failing to live up to the hype, even if they weren't neccessarily the worst bouts when viewed without context.
So without further ado, here are the top ten most disappointing fights in UFC history.
10. Frank Mir vs. Mirko Cro Cop
UFC 119, September 25 2010
Heavyweight MMA has followed a pretty clear algorithm since the beginning of the sport - if the fight doesn't end in a finish within the opening round, it's likely going to be an absolute chore to sit through.
There are occasional exceptions to the rule, mostly when the few truly elite heavyweights enter the cage or ring, but for the most part, if a heavyweight fight passes the five minute mark you're unlikely to be entertained save for a random finish that puts an end to the sloppy scrap.
Originally scheduled to face Antonio Rodrigo Nogueira for the second time, Frank Mir instead saw himself take on a replacement in another PRIDE heavyweight legend, Mirko Cro Cop at UFC 119.
It may not have been the strongest PPV card ever, but it was headlined by two legends with massive name value that, although neither was considered in their "prime" anymore, were both regularly exciting.
The former UFC heavyweight champion Mir was coming off a brutal loss at the monstrous hands of Shane Carwin and was looking to bounce back after once again getting mauled by a bigger, stronger athlete, his 72-second shellacking of Cheick Kongo sandwiched between tough losses to Brock Lesnar and the afforementioned Carwin.
While he may not have had a lot of momentum, Mir could always be counted on to deliver a quick and exciting fight - the only time he had ever even seen a third round was a fight back in 2006 when Mir had returned following a devastating leg injury and was in horrendous shape - all of his other bouts, win or lose, ended in a finish within two rounds (often within two minutes) whether it be via knockout or from one of his legendary, bone-breaking submissions.
Mirko Cro Cop on the other hand was seemingly in the midst of one of his career resurgences, having won four of his last five fights (all by form of finish). His recent wins included an epic kickboxing battle with Pat Barry and his lone loss came at the hands of future heavyweight champion Junior Dos Santos thanks to a broken orbital bone.
The PRIDE legend's resume truly spoke for itself and he always delivered action for the fans.
Mirko was one of the rare breed of athletic heavyweights that could still fight well even a round or two into a bout, and of course his highlight reel of knockouts was legendary for a reason - whether he was head kicking Igor Vovchanchyn, Alexander Emilianenko, and Wanderlei Silva, smashing the likes of Mark Coleman and Josh Barnett with his fists, or engaging Fedor Emilianenko in what many regard as the greatest fight of the prior decade, the Croatian kickboxer was always a special treat to watch perform.
And then the main event of UFC 119 happened.
Mir looked in better shape than his last two outings, where he had beefed up his frame to almost comical levels that as a result left him nearly immobile, showing off solid defense when Mirko opened up in the early seconds.
And then little else happened for over 13 minutes.
Both men seemed to respect the power the other possessed and as such appeared extremely timid, each hoping for the other man to make a costly mistake and refusing to be the one to go first.
Mir's attempts to take the fight to the mat were unsuccessful thanks to his rather lackluster wrestling and Cro Cop's excellent takedown defense, leaving the two heavyweights in the clinch for extended periods where neither man did much of anything. At range, it was essentially a staring contest.
The crowd quickly lost their patience, showering the two legends with boos as the minutes ticked by. Somehow, despite the tepid pace and his utter lack of output, Mir was breathing heavy and appeared to be tired (it was a heavyweight fight that made it past the first round after all), though Mirko did little to exploit it.
With about two minutes left in the three-round main event, fans had already started pouring out the exits, annoyed they had stuck around for such a disappointing headlining act.
And then with about one minute left in the fight, Cro Cop pressed the action and looked to land his left hand out of a clinch; instead, pulling Mirko's head down via a single collar tie, Mir delivered a vicious knee to Cro Cop's chin that sent the legend crashing to the canvas.
It was a brutal knockout that did little to make up for the previous fourteen minutes of inaction, and in fact made it an even sadder outcome for those in attendance (at least the ones that were still in the arena) - seeing the aging warrior knocked dead in the dying seconds of a horribly boring fight was not what anyone was hoping to see.
9. Ken Shamrock vs. Dan Severn II
UFC 9, May 17 1996
If you asked a few UFC fans that have been following the sport since its early days what the worst UFC main event of all time was, odds are at least one of them will bring up Ken Shamrock vs. Dan Severn II.
Back in the very early days of the UFC, individual match-ups didn't have a lot of build-up thanks to the tournament format, but the advent of a "Superfight Championship" starting at UFC 5 changed that and added a more boxing-esque quality to the promotion courtesy of non-tournament bouts between two established names headlining an event and drawing in viewers.
Ken Shamrock, an early star in the sport as well as in pro wrestling who had lost to Royce Gracie at UFC 1 and made it to the finals of UFC 3 before an injury saw him withdraw from the tournament, took part in the very first "Superfight" in MMA history - a rematch between himself and the winner of UFC 1, 2, and 4 (and similarly a competitor at UFC 3 who withdrew due to injury), Royce Gracie.
After a draw saw the new belt left undeclared and Gracie leaving the sport for a while, Shamrock was given a second crack at the "Superfight" title against the runner-up of UFC 4 and the winner of UFC 5, Dan Severn.
This time Shamrock would emerge victorious in just over two minutes via a guillotine choke in a fun scrap which included Severn hitting a beautiful suplex early on.
Shamrock would fight to another draw in his next Superfight against Oleg Taktarov before tapping out Kimo Leopoldo in his next outing; Severn on the other hand would become just the second man to win multiple UFC tournaments by winning the "Ultimate Ultimate 1995" event, earning himself a rematch with Shamrock.
The Superfight at UFC 9 captured the attention of the early MMA world and fans were expecting another exciting scrap between the two, but unfortunately legal problems would end up turning the highly anticipated match-up into one of the most bizarre and terrible fights in UFC history.
Taking place in Detroit, Michigan and dealing with mounting political and media pressure given the sport's early reputation as "human cockfighting", the UFC's owners were stuck in a battle in the courtroom as lawmakers in Detroit moved to stop the event from taking place just days before the event.
At the eleventh hour, the event was allowed to go on but with some rather restrictive new rules in place - including the complete banning of strikes to the head with either closed fists or headbutts, with the Michigan Athletic Commission promising to arrest any fighter who violated these rules.
To make matters worse, kicks were also banned if the fighters decided to wear shoes for their bouts. Given that both Shamrock and Severn were wrestlers, both opted to lace up their wrestling shoes and as a result limited their offensive arsenal even further.
Now a bout with those kind of crippling restrictions (especially on such late notice) is sure to be a dud, but that's not something fans knew about before sitting down to watch the pay-per-view. What they were promised was a no-holds barred fight between two of the toughest fighters on the planet - what they got was one of the most disappointing "fights" they could imagine.
Surely wanting to avoid another submission loss, the superior wrestler Severn opted to avoid grappling for almost the entire 30-minute affair, instead choosing to engage with Shamrock in what amounted to a glorified staring contest.
For half an hour two of the "baddest men on the planet" gazed into each other's eyes and circled around the Octagon, occasionally throwing open handed slaps at each other before returning to their incredibly dull dance.
Near the end of the fight Severn finally had enough and took down Shamrock, landing a few strikes (closed fists to boot...luckily, he wasn't arrested) before the horn sounded and ultimately earned himself a decision "victory".
The fight was truly a product of its time and one can't help but feel extremely sorry for any poor sap that spent their hard-earned money back in 1996 on this travesty of a fight.
8. Vitor Belfort vs. Randy Couture II
UFC 46, January 31 2004
UFC 46 was a massive event at a time when the UFC was struggling to survive.
In addition to a highly anticipated rematch between Frank Mir and Wes Sims (the first fight saw Sims disqualified for illegally stomping on Mir's face, repeatedly and while grabbing the cage no less), the man everyone considered to be the best lightweight in the world was moving up to challenge longtime welterweight kingpin Matt Hughes for this throne. Even the prelims would prove memorable, with future GOAT Georges St. Pierre making his UFC debut that night.
To top off the impressive card, early UFC star Vitor Belfort would finally look to realize his potential as he sought to dethrone the light heavyweight champion Randy Couture, the former heavyweight champ and the man who handed Vitor Belfort the first loss of his career back at UFC 15.
Since Couture grounded and finished the young Brazilian phenom in 1997, "The Natural" had experienced both the highs and lows of the sport. Posting a record of 7-5 at heavyweight, Couture went on to capture and defend the UFC heavyweight title before subsequently losing it to Josh Barnett, who would later be stripped due to a failed drug test; Couture would then lose against Ricco Rodriguez in his attempt to reclaim the vacant title.
At 38 years of age, many wrote Randy off and expected the Olympian wrestler to retire or fade into obscurity. Instead, given his roughly 220lb frame which was tiny for a heavyweight, Couture opted to drop down to his natural weight class of light heavyweight.
Couture would be paired up with rising star Chuck Liddell for an interim championship given Tito Ortiz's reluctance to fight his "friend" Liddell, the interim belt on the line in the UFC's effort to force champion Ortiz into accepting a fight with "The Iceman". To everyone's surprise, Couture dominated Liddell en route to a third round TKO.
Randy would then decimate Tito Ortiz over the course of five rounds to emphatically capture the undisputed light heavyweight title, making him the first fighter in UFC history to capture undisputed titles in two different weight classes.
After having his air of invincibility shattered by Couture, Vitor would rebound with an easy submission win before scoring arguably the most famous knockout in the old days of the UFC - a 44-second blitzing of Wanderlei Silva during the UFC's first trip to Brazil that showcased the Phenom's incredible hand speed.
Belfort would then accept a lucrative offer from PRIDE, where he would post an impressive 4-1 record at heavyweight before the UFC lured him back stateside. Originally slated to fight Tito Ortiz for the title at UFC 33, injuries kept Vitor sidelined until he was matched up with the UFC's latest rising prospect in Chuck Liddell.
Belfort accounted well for himself in the fun 15-minute scrap but ended up losing a decision in his return to the Octagon, derailing his hopes for a title shot.
A year later he would return in emphatic fashion and remind everyone of his vicious finishing ability by absolutely trouncing Marvin Eastman, opening a disgustingly large cut over Marvin's right eyebrow that looked as if it were opened by a hatchet.
With Couture having already defeated Liddell and Ortiz, the stage was set for a massive rematch early in 2004 against the next top contender; would Couture's wrestling, dirty boxing and tactical brilliance get the job done once more, or would a more seasoned Belfort be able to realize his full potential and use his incredible athletic ability to earn himself the title and redemption?
Just as hype surrounding the bout was reaching a fever pitch, disaster struck as Vitor's sister Priscila went missing mere weeks before UFC 46.
As time went by it was suspected that she was kidnapped to be held for ransom given Belfort's status in Brazil, but the family received no ransom calls or other information, leaving what happened to her a mystery (in 2007 a woman admitted to her involvement in Priscila's botched kidnapping and murder, but her remains were never recovered from the supposed burial site leaving a definitive answer to her disappearance unknown to this day).
Despite the tragic circumstances, Belfort vowed to fight on and use the exposure of his fight to raise awareness for his missing sister, adding even more weight to the massive UFC 46 main event.
The rematch seven years in the making began with Couture closing the distance and looking to trap Vitor against the cage, with a left hand narrowly grazing him on the way in to the clinch. Vitor secured double underhooks and pinned Randy against the cage, only for the commentators (along with Vitor and shortly after the referee) to notice Randy wincing in pain and clearly having trouble with his eye.
Referee Big John McCarthy called a stop to the action and brought in a doctor, and it soon became clear that Vitor's left hook had grazed Couture's eye, the seam of his glove opening up a cut directly on Randy's eyelid.
Given the placement of the cut and the dangers it posed, the doctor called the fight and given the cut was caused by a punch and therefore a legal blow, Belfort was declared the winner.
While it was too short to be called a bad fight like many of the entries on this list, it was essentially no fight at all and answered exactly zero questions that fans had heading into the contest, ending what was otherwise a fantastic event on a down note even if seeing Vitor get the belt wrapped around his waist amidst all the turmoil he was going through was a touching moment.
7. Anderson Silva vs. Demian Maia
UFC 112, April 10 2010
Anderson "The Spider" Silva was at the height of his powers heading into the UFC's first ever trip to Abu Dhabi at UFC 112.
Having captured the middleweight title shortly after entering the UFC and defended the belt in dominant fashion five times already, as well as having two quick knockouts up at light heavyweight to his name and eight post-fight bonus awards in his ten Octagon appearances, the Spider was seen as an untouchable assassin designed to entertain the masses with his stellar defense, impressive Brazilian jiu-jitsu skills, and vicious Muay Thai.
His incredibly entertaining fighting style had recently given way to an incredibly frustrating and tiresome fight at UFC 97 however, where Anderson seemed content to play with his wildly overmatched foe for 25-minutes as renowned jiu-jitsu artist Thales Leites tried desperately to bring the fight to the floor and failed repeatedly, yet was hardly punished by the dominant champion.
The dismal performance drew the ire of the fans but his next outing quickly erased everyone's memory - moving up for another one-off fight at light heavyweight, Silva took on recent 205 pound champion Forrest Griffin at UFC 101.
The massively hyped fight had many believing the Spider may have bitten off more than he could chew given Griffin's size and highly underrated grappling abilities, but those beliefs were quickly silenced when the two entered the cage in Philadelphia.
Anderson danced around his lumbering foe as if he was in The Matrix, effortlessly dodging Griffin's strikes and landing precision counters in what can only be described as one of the most embarassing emasculations in UFC history. Griffin was dropped three times in the span of just over three minutes before the fight was stopped and to make matters worse, proceeded to run out of the cage following the fight.
The shocking dominance reminded the world what kind of otherworldly talent Anderson was and any memories of his tepid UFC 97 performance were immediately erased.
Slated to face off against Vitor Belfort early in 2010, an injury and a slower-than-expected recovery delayed the fight twice until April. Just weeks out from the UFC's historic trip to the Middle East, Vitor Belfort then injured his shoulder in training and was forced to pull out of his title shot; due to the next top challenger not being medically cleared to compete so soon after a recent bout, in stepped fellow Brazilian Demian Maia to save the day.
The 12-1 BJJ ace was easily one of the most accomplished Brazilian jiu-jitsu competitors to ever make the transition to MMA. Sporting a submission game unlike anyone in the sport, Maia had finished all but one of his wins and had already bounced back from his lone career defeat (a 21-second knockout loss) with a dominant decision victory.
Maia was certainly an interesting fighter and one to keep an eye on, but fans weren't exactly high on his prospects against the middleweight king heading into UFC 112.
Though his jiu-jitsu was otherworldly, his wrestling game had proven to be rather weak at the time and he held little chance of getting Silva down to the floor, especially on such short notice without having any time to really work on that aspect of his game.
Though he was learning the other aspects of the sport, Demian was a specialist through and through - his striking wasn't exactly what you'd call good, and considering he was going up against the best striker the UFC had ever seen, he was destined for an ass-kicking.
What virtually every fan had forgotten about was Silva's last fight against a man stylistically indentical to Maia.
Thales Leites was an extremely accomplished BJJ expert himself and also lacked much of a striking game at the time of his title shot at UFC 97. Despite being clearly outclassed by the Spider, he managed to survive 25-minutes without taking much damage simply by failing to get takedowns then proceeding to scoot around on his butt while Silva walked away or taunted him.
Given the heat Anderson had taken following that performance, and the adoration he had received for the brilliance he had put on display against Griffin, combined with the opportunity to showcase his talent to an entirely new market for the UFC's potentially lucrative new expansion? There was no way Silva would do something like that again.
But then he did.
Rather than dominating and finishing his clearly outgunned opponent on the feet, Silva effortlessly shucked off Maia's takedowns and attempts to pull guard, then proceeded to taunt him and run around the cage.
Occasionally throwing a hard leg kick or a bizarre strike amidst his taunts, Silva treated his massive main event gig as a playful sparring match. The entire fight was extremely frustrating for fans, especially given his abilities and that the co-main event had disappointed just before Silva made his walk; it was one thing for Silva to taunt his opponents, it was another to transform his entire performance into a circus act.
Now the fight would have featured even higher were it not for the fact that it had some funny moments and it's genuinely hilarious looking back at some of the ridiculous stuff Silva was doing in the middle of a UFC title fight, with absolutely no regard for the repercussions.
Whether he was standing still and begging Maia to hit him, backing Demian up with what looked like an epileptic dance routine, playing an air guitar, or trying to hide behind the ref, Silva dutifully played the part of a comedian at UFC 112.
Unfortunately for fans that had wanted to see a fight, Silva's performance was not a good one and it drew the wrath of Dana White, who promised Silva would never headline a card again (thankfully he didn't keep his word on that one) and said it was the most embarassing thing he'd seen in all his time in the sport.
Abu Dhabi didn't take too kindly too it either, with Silva's antics not going over well with the locals and damaging the brand in the region, with the UFC not returning to the Middle East for years following the debacle.
The very public backlash against his performance would have one assuming Silva learned his lesson, but he hasn't had to fight another BJJ specialist since, so we may never know if circus Silva truly died that night or he simply hasn't had a chance to return.
6. Derrick Lewis vs. Francis Ngannou
UFC 226, July 7 2018
If you were to ask a handful of MMA fans before UFC 226 what fight on the card was for sure not going to the judges' scorecards, the co-main event between Derrick Lewis and Francis Ngannou would have been the only answer you'd have received.
This was a match-up between two of the scariest and most vicious knockout artists in the heavyweight division, two massive (albeit with very different builds) power punchers that could fell a rhino with a single strike. While the superfight between heavyweight champ Stipe Miocic and light heavyweight king Daniel Cormier took top billing that night, the battle of the beasts was just as highly anticipated amongst fans and for good reason.
A developing standout from Cameroon, Francis Ngannou was a sizeable favourite heading into their massive clash at UFC 226. Despite coming off a loss in his title bid to Stipe Miocic, the "Predator" was still the most feared man in the division - his raw power and strength are second to none, and with the valuable experience he'd gained in his failed title shot he had undoubtedly become even more deadly.
After a decision loss in just his second pro fight, Ngannou tore through ten straight opponents, finishing all eleven of his career victories in ten minutes or less, with six of his victims coming in the Octagon. He had mauled Curtis Blaydes, smashed Andrei Arlovski, and positively murdered Alistair Overeem during his run for the heavyweight strap; in his highly anticipated title shot at UFC 220 however, Ngannou's inexperience cost him dearly as he discarded the patient counter-punching style that had gotten him there and instead went all out for the kill in the opening round.
Miocic being the savvy and durable champion that he is, weathered the early storm and stuck to a wrestling-heavy gameplan, wearing out his bigger foe and exposing Ngannou's weak grappling. Although he had little in terms of technique on the floor, Ngannou's athleticism and strength still allowed him to continuously get up off the canvas, Miocic forced to accept less dominant positions and patter away with light shots en route to a grinding decision victory.
Despite coming up short, Ngannou's raw ability was apparent and the Miocic fight served as a perfect learning experience for the developing fighter, particularly in teaching him that raw power alone isn't always enough.
On the other side of the Octagon would be the "Black Beast", Derrick Lewis.
Lewis is a gargantuan heavyweight with absolutely ridiculous power and explosiveness despite having a much less athletic (in appearance) figure than the likes of Ngannou. Lewis sported a 19-5 record having finished all but one of his opponents (the ridiculously durable Roy Nelson) and, save for two decision losses early in his career, all three of his more recent losses had come via form of knockout as well.
He was an honest-to-goodness brawler that could match Ngannou's size and punching power and wasn't afraid to throw his hands against anyone, as shown by his nasty knockouts over the likes of Guto Inocente, Gabriel Gonzaga, and Travis Browne.
The match-up had fireworks written all over it and as a result the fans were all up out of their seats when the two big hitters entered the cage...but what ensued was not what anyone had expected.
Rather than returning to his more patient approach and learning from his mistakes in the Stipe fight as most expected, Francis became a little too patient and instead was completely gunshy, unwilling to throw virtually anything at all.
Lewis on the other hand quickly picked up on his opponent's timidity and took advantage in the most conservative way possible, landing some leg kicks at a distance and throwing an occasional punch to do just enough to "win" the rounds on the scorecards without awakening the slumbering beast.
As a result one of the most boring 15-minute fights you'll ever witness went down inside the Octagon, virtually nothing of note occuring over its duration as Lewis cruised to an easy decision victory filled with lots of intense staring and little else.
The crowd voiced their displeasure throughout the tepid staring contest but to little avail - the two beasts just didn't show up that night and there was nothing they could do to change it.
Luckily both men would bounce back and return to form in their future fights, but that does little to erase the memory of one of the most uneventful fights in UFC history.
5. Tim Sylvia vs. Andrei Arlovski III
UFC 61, July 8 2006
Now in retrospect newer fans may question how a fight involving Tim Sylvia could rank so highly on this list, but that would be completely ignoring his earlier career and place in the heavyweight division back in the day.
Unlike some of the ill-advised trilogy bouts in MMA's history, Andrei Arlovski's third bout with Tim Sylvia had all the makings of a classic.
The 6'8 "Maine-iac" Sylvia may have had some embarassing moments later in his career, but at one point in time he was one of the most dangerous fighters on the planet.
The massive Miletich-trained standout racked up an impressive 13-0 record with just two decisions (one being against the incredibly durable Ben Rothwell) before getting his spot in the UFC, where he beat the brakes off of the unskilled but tough Wesley "Cabbage" Correira.
A title shot (the heavyweight division was rather thin back then) followed and Sylvia smashed early UFC pioneer Ricco Rodriguez to earn himself the heavyweight title - a quick defense against Gan McGee however soon turned into a disaster as Sylvia failed his post-fight drug test for an anabolic steroid and was subsequently stripped of his UFC belt.
After serving his suspension, Sylvia would fight a young Frank Mir for the vacant title and famously had his forearm snapped in half by the submission specialist in under a minute.
Tim bounced back with a knockout over Wes Sims in a smaller promotion before being brought back into the UFC to fight a surging Belarussian named Andrei Arlovski, this time for an interim heavyweight title due to Frank Mir's injury hiatus following a devastating motorcycle accident.
Arlovski had shown to be a devastating knockout artist in his own right, the chiselled 6'4 "Pitbull" sporting impressive athleticism (especially for a heavyweight), a missile for a right right hand and a surprisingly competent submission game thanks to his background in Sambo. Unfortunately he also had a glaring weakness - his rather fragile chin.
All ten of Arlovski's fights to that point had ended with a finish, Arlovski being on the receiving end of three of those finishes (all by knockout). After having been knocked out in back-to-back fights against Ricco Rodriguez and Pedro Rizzo, many had already written off the once-promising prospect, but Arlovski would bounce back with two quick knockouts of his own, including one over Vladimir Matyushenko.
Heading into their interim title tilt, fans were split on who would emerge the victor; Sylvia would likely hold an edge on the feet given Arlovski's suspect chin, but Andrei's submission skills would give him a big edge on the mat. Just seconds into their first meeting, Arlovski showed off the dangers that the "cannon" aspect of a glass cannon presents, sitting Sylvia down with a massive right hand before snatching up a rare achilles lock to capture the interim crown in just 47 seconds.
Arlovski proceeded to smash another poor victim before Mir's extended injury layoff forced the UFC to strip the champion of his belt and promote Arlovski to the undisputed heavyweight king.
He emphatically defended his throne with a blistering 15-second knockout of Paul Buentello, a short and precise right hand instantly shutting the challenger's lights off and actually causing him to faceplant directly onto Arlovski's back.
Sylvia meanwhile had worked his way back to a title shot and a chance at redemption courtesy of a three-fight winning streak, which included a brutal head kick knockout over Tra Telligman.
Having seemingly entered his prime, Arlovski entered his second meeting with Sylvia as a massive favourite, with few seeing Sylvia as standing a chance against the iron-fisted ruler of the heavyweight division.
If there's ever an example of how quickly people can forget about a fighter's shortcomings, it would be Sylvia-Arlovski II.
Arlovski looked to smash his rival with the same nuclear right hand that had earned him so many knockouts before - unfortunately his predictable attack cost him dearly as midway through the first round Sylvia landed a short uppercut counter as the champion blitzed him. Follow-up shots had the mid-2000's premier glass cannon out cold facedown on the canvas, his title reign over in a flash.
With the two heavyweights having a clear edge over the rest of the division at the time and both now holding quick finishes over the other, a rubber-match to determine the clear king of the UFC's heavyweight division was a no-brainer.
And so just two months later the two heavyweights would step into the Octagon for a third meeting, this time headlining a massive UFC 61 pay-per-view which also featured a highly anticipated grudge match between Tito Ortiz and Ken Shamrock.
The card set new buyrate records for the UFC with over 750,000 PPV buys and came in second for the highest gate in UFC history at the time; thanks to a controversial stoppage early in the Ortiz-Shamrock rematch and a few other disappointing fights, fans turned to the heavyweight title trilogy bout to save the day.
Surely a heavyweight scrap between Sylvia, who had gone to a decision just three times in 23 fights and Arlovski, who had never gone to the judges' scorecards in his 14-fight career, would provide ample fireworks just like their last two match-ups?
It turns out, when two fighters who have been finished quickly by their rival and have everything to lose square off, sometimes they'll be wary of doing...just about anything.
Both men refused to engage in anything meaningful, instead content to simply throw safe and non-commital strikes for the entirety of the five round affair. Instead of another quick heavyweight kill, fans were treated to 25-minutes of light sparring that was about as memorable as watching paint dry.
And so remains the old MMA-viewing adage - if a heavyweight fight makes it out of the first round, odds are you aren't going to be enjoying what you see.
4. Israel Adesanya vs. Yoel Romero
UFC 248, March 7 2020
Here we have the inspiration for this article - Israel Adesanya's last fight.
Although Yoel Romero was coming off of two losses heading into the main event of UFC 248 (albeit both extremely close and controversial decisions), the match-up between the 42-year-old Cuban Olympian and the undefeated champion Israel Adesanya captured the fervor of the MMA fanbase like few fights could.
Romero has been a fan-favourite since he began in the UFC thanks to his mystifying athleticism and incredible talent, turning himself into one of the most feared knockout artists in the sport despite coming from an entirely grappling background - in fact, Romero rarely used his Olympic silver medal-winning wrestling other than to defend takedowns and occasionally mix in an explosive takedown to keep his opponents guessing, instead preferring to stand and trade with his opposition.
Unlike some of the other exciting knockout artists on the roster, Romero is somewhat of an anomaly - he isn't a fighter that relentlessly charges forward until his victim falls, or a fighter that looks to counter with a massive bomb, or even a fighter all that interested in scoring points; instead he is a master of lulling his opponents into a tense and slow-paced affair, biding his time and determining the best opportunity to strike before exploding in furious blitzes.
Now this can often lead to extended periods of inactivity in his fights, where Yoel turns into an almost-entirely defensive creature, using his incredible reflexes and effective (if sometimes awkward) striking defense to limit his opponent's effectiveness while doing little in return.
And then he explodes.
When he does, his opponents often wake up looking up at the ring lights, and if they do manage to survive one of Romero's trademark blitzes, Yoel has typically scored damaging shots that regularly make up for his lack of activity thanks to his ability to inflict so much damage in short windows of opportunity.
Romero had racked up devastating knockouts over the likes of Clifford Starks, Ronny Markes, Derek Brunson, Tim Kennedy, Lyoto Machida, Chris Weidman, and Luke Rockhold over his UFC tenure, often scoring his finishes in the third round (all of the above finishes came in the third with the exception of Starks). All three of his losses meanwhile came in extremely close decisions - two to Robert Whittaker and one to Paulo Costa - with all three of those bouts winning fight of the night honours.
His second bout with Whittaker and his most recent fight against Costa both featured highly controversial decisions.
Nearly everyone but the judges had scored his rematch with Whittaker in favour of Romero thanks to his extremely damaging bursts that nearly finished the champion on multiple occasions, with very strong arguments for the Cuban earning not one but two 10-8 rounds over the course of the five round war.
The fight with Costa had fans torn on the true winner of the contest, with Romero taking the third stanza and the second round being the deciding factor with many scoring it in Romero's favour.
Regardless of whether or not he had deserved to win those two fights, the bouts themselves were both extremely entertaining and despite not getting the finish, Romero's sequences of violence provided more than enough excitement throughout the memorable scraps.
Adesanya on the other hand was riding high off of his masterful destruction of highly regarded middleweight champion Robert Whittaker at UFC 243, and 2019's epic Fight of the Year winner which saw Adesanya capture the interim title against Kelvin Gastelum in a thrilling five-round war.
The undefeated champion's prowess on the feet thanks to his stellar kickboxing background and lethal accuracy, combined with his flashy style and personality, had turned Israel into a star for the UFC as he ascended the ranks, besting the likes of Brad Tavares and Anderson Silva while finishing fighters like Derek Brunson with disturbing ease.
After capturing the title in dominant fashion against Whittaker, Adesanya had all the makings of a bonafide superstar, and after an injury to top contender Paulo Costa, fans were equally delighted to see Adesanya matched up with the Cuban missile Yoel Romero.
Adesanya's precision and patience seemed like the perfect foil for Romero's explosive style, but the Cuban's mastery of controlling the tempo of a fight, lulling his opponent's to sleep with feints and setting up traps he'd exploit later in fights, and his absolutely freakish athleticism made Romero arguably the stiffest test of Adesanya's 18-fight career.
The hype surrounding the fight earlier this year was positively massive and a big win for the new champion would surely catapult him into superstardom...
And then the fight happened.
Some early shenanigans from Romero put viewers in a good mood as the vet looked to disarm his foe, but unfortunately for fans it worked a little too well - Adesanya smartly avoided giving Romero any opportunities to counter, and what resulted was a lot of staring and very little fighting.
A big right hand counter in the first caught Adesanya's attention and made Adesanya even more reluctant to engage from then on - the entire first round saw just two strikes landed by the champion and a total of four from the challenger, with less than twenty strike attempts combined over the first five minutes.
The pace didn't pick up much as time went on, with Romero occasionally charging forward only for Adesanya to turn tail and quite literally run from his assailant. Israel in return would land a leg kick or two every once in a while, which is essentially what secured him the highly controversial decision victory - though Adesanya ended up landing a few more total strikes, with how few were thrown and landed on both sides many fans argued Romero's more significant shots and comparative aggressiveness should have earned him the decision.
The five round non-fight put everyone to sleep and had many fans turn sour on the brash champion, particularly given his pre-fight trash talk that fell flat given he quite literally ran away from his opponent.
It was a tremendously disappointing title "fight" that looked even worse given the absolute war that preceeded it courtesy of Weili Zhang and Joanna Jędrzejczyk; after seeing a clear Fight of the Year contender, nobody wanted to have their adrenaline dumped by a horrendous staring contest, but unfortunately for fight fans that's exactly what happened at UFC 248.
3. Rashad Evans vs. Rampage Jackson
UFC 114, May 29 2010
Unlike the other bouts on this list, there was no title on the line nor did either fighter sport an astronomically high finishing rate (though both had earned their fair share of highlight reel knockouts, Rampage in particular) - and yet the hype surrounding their three round fight in 2010 was absolutely insane.
To understand at least somewhat why so much buzz surrounded their clash at UFC 114, one must take a look at the two personalities involved and all the drama that unfolded before the Octagon cage door shut behind them.
Quinton "Rampage" Jackson cut his teeth on the regional circuit in the US since his MMA debut in 1999, utilizing his raw strength and high school wrestling credentials to post an impressive 10-1 record before heading overseas to the flourishing Japanese MMA juggernaut PRIDE FC.
After losing his promotional debut via submission to the legendary Kazushi Sakuraba, Rampage would become a staple in the organization, known for his entertaining fighting style, his raw power, his affinity for slamming people, and his genuinely hilarious personality.
Rampage would win seven of his next eight bouts with his lone loss coming via a DQ due to a groin strike, earning his spot into the PRIDE 2003 Middleweight (the equivalent of light heavyweight in the US) Grand Prix.
Jackson defeated Murilo Bustamante to advance to the semi-finals where then met the UFC's budding star Chuck Liddell, who was entered into the tournament by UFC president Dana White in the promotion's bid to prove their fighters were superior to PRIDE's.
Fans of both organizations expected Chuck Liddell and PRIDE champion Wanderlei Silva to meet up in the finals for a highly anticipated superfight, but the two had to get through their respective quarter- and semi-final bouts to make that dream match-up come true.
Rampage spoiled the UFC and fans' plans by battering the Iceman before finishing him with knees to the head on the ground (perfectly legal in PRIDE) in the second round, sending the UFC home empty handed. Unfortunately for Rampage, Wanderlei Silva held up his end of the bargain and proceeded to trounce his prey to win the Grand Prix in style.
The heavy-handed star would continue his success with the promotion regardless, posting a 5-2 record in the coming years which includes one of the most vicious knockouts in MMA history, his savage slam KO of Ricardo Arona. His two losses came in a rematch with his rival Wanderlei, and at the hands of Silva's stablemate and PRIDE 2005 Grand Prix champion Shogun Rua.
Following his loss to Shogun, Jackson would win three straight before signing with the UFC, immediately making his presence known courtesy of a crushing knockout of Marvin Eastman; given his prior victory over Chuck Liddell in 2003 and Liddell running out of opponents to demolish during his epic title reign, Rampage was thrust into a title fight in just his second UFC appearance.
Regardless of once again being the underdog against the UFC's biggest star, Jackson ended Liddell's legendary title reign in less than two minutes with a vicious right hook to become the UFC light heavyweight champion at UFC 71.
Following the UFC's acquisition of PRIDE in 2007, Rampage would unify the UFC and PRIDE titles with a decision win over Dan Henderson, the last PRIDE middleweight champion.
For his next defense, Rampage would take on an unlikely challenger in The Ultimate Fighter's Forrest Griffin, a gritty blue-collar fighter who had gone from winning the UFC's wildly successful reality show to becoming a bonafide title contender courtesy of a massive upset victory over Shogun Rua.
The two would coach opposite one another on the seventh season of The Ultimate Fighter, earning each other's respect during the show and ultimately turning in a rather tame installment of the show that often featured heated rivalries between coaches.
Early on in their title tilt it appeared as though Griffin's cindarella story was coming to its expected conclusion as Rampage dropped the challenger with an uppercut and nearly finished the perennial underdog, but Griffin managed to survive the early scare and began to put the pace on the champion.
Griffin would stick to a disciplined gameplan for the remainder of the five round battle, hammering Rampage with heavy leg kicks (setting a UFC record for most leg kicks landed in a fight in the process) and generally outworking the champion en route to another shocking upset victory.
Rampage would bounce back in a trilogy bout with his old rival Wanderlei Silva, finally getting on the board and earning his revenge courtesy of an absolutely disgusting counter left hook. He would then defeat Keith Jardine to earn a promised shot at the UFC light heavyweight title opposite Rashad Evans, but lingering injuries would delay Quinton's return to the cage and that shot went to Lyoto Machida instead.
Rashad Evans on the other hand was a UFC staple since the early days of his MMA career - having competed as a heavyweight on the second season of the UFC's smash hit The Ultimate Fighter, Rashad defied expectations by winning the season despite being vastly undersized for the division and normally competing at 205 pounds.
Following his successful stint on the show, Rashad would return to his more natural light heavyweight form and rack up wins, propelling himself into the upper echelon of the division with vicious knockouts over Jason Lambert and Sean Salmon. A step up in competition saw Rashad take part in a rare draw against Tito Ortiz before he handed fellow undefeated prospect and TUF 3 winner Michael Bisping the first loss of his career (albeit in an extremely controversial decision).
The 12-0-1 NCAA Division I wrestler was then paired up with the "Iceman" Chuck Liddell.
The living legend had suffered back-to-back losses for the first time in his career, losing his title in the process, before rebounding with an incredible win over fellow legend Wanderlei Silva in 2007's Fight of the Year. Fans were ecstatic that the Iceman was back and Rashad Evans was the unfortunate soul who had to get iced on Liddell's path back to the title.
After a largely forgettable first round, Liddell began opening up in the second, stalking Evans as Rashad looked for an opportunity to counter. Looking for a heavy uppercut, Liddell had his hands down and never even saw the lightning-quick right hand that sent him to the netherrealm.
The incredible knockout over a resurgent Liddell and his sterling record made it a no-brainer for the UFC to give Rashad Evans a crack at the light heavyweight title.
Facing the TUF winner that preceeded him in a fun back-and-forth fight, Evans demolished Forrest Griffin in the third round via nasty ground and pound to capture the light heavyweight title and end Forrest's cindarella title reign before it had a chance to really begin.
His first title defense was expected to be against Rampage Jackson, but injuries delayed Jackson's shot and instead one of the most intriguing and unique fighters in the sport, the 14-0 "Dragon" Lyoto Machida, would fight for the title instead in what would be the first title fight in modern UFC history between two undefeated fighters.
Unfortunately for Rashad, the puzzle that was Machida remained unsolved at UFC 98 as the Brazilian karateka absolutely destroyed the champion with disturbing ease.
Rather than having Jackson face Machida upon his return, the UFC opted to utilize the star power of Rampage and Rashad and their mutual dislike of each other to headline their tenth season of The Ultimate Fighter, a series both men had great familiarity with already.
In addition to the star power the coaches would bring, the UFC gave Youtube sensation Kimbo Slice (aka Kevin Ferguson) a chance to earn his way into the UFC by competing on the show. The backyard brawler and 3-1 MMA fighter had tremendous worldwide recognition thanks to his filmed backyard fights that had gone viral over the previous few years, and despite his rather lacking pro experience Slice brought in absolutely massive ratings for the entire season.
In addition to seeing Slice, fans were enthralled by the rapidly growing rivalry between Jackson and Evans - the two were constantly at each other's throats, incessantly talking trash to each other and nearly coming to blows on multiple occasions throughout the filming of the show.
Scheduled to compete against one another at the end of 2009, things soon fell apart as Rampage was cast to play B.A. Baracus in The A-Team remake, Rampage opting to postpone the fight in order to play his dream role, much to the dismay of the UFC and the fans.
The move sparked outcry from fans everywhere and drew the ire of the UFC, with Rampage at one point stating that he was retiring from the sport due to "mistreatment" from the UFC. Eventually cooler heads would prevail and Jackson would return to the sport, but first Evans would defeat a replacement opponent in Thiago Silva by decision to keep the showdown's hype alive.
After several more agonizing months of waiting for the highly anticipated grudge match to happen, the two finally stepped into the cage at UFC 114 in May of 2010, their rivalry propelling the otherwise light pay-per-view offering to well over one million buys.
The massive fight started off in shocking fashion as Rashad burst out of the gate, staggering Rampage with a right hand before charging him into the fence.
And then the excitement slowly left the building.
Rather than an intense battle or stunning knockout that the fans expected, Evans turned the fight largely into a wrestling match and unfortunately not a very entertaining one.
What was supposed to be the culmination of over a year of hype and excitement ended up being a fifteen minute slog.
Now to be fair, it did have a few moments aside from the opening exchange - Rashad landed a few nice takedowns, Rampage wobbled Rashad in the third to provide some last-minute drama - but considering the amount of hype that the bout had behind it, and how long fans had to wait to see it, seeing Rashad grind out a dull decision with the two men spending most of the fight clinching against the cage was exactly the last thing that anyone wanted to see.
At least this fight occurred back when non-title main events were still just three rounds.
2. Junior Dos Santos vs. Cain Velasquez I
UFC on Fox 1, November 12 2011
Now this is a very unique entry on this list because it really wasn't a bad fight whatsoever - it's hard to call a quick knockout without a constroversial stoppage or other controversy a bad fight - but instead earns its spot on this list because of how much the UFC and the sport had riding on a very different fight.
From the time the two heavyweights debuted in the UFC in 2008 to the time they first met in the Octagon late in 2011, Cain Velasquez and Junior Dos Santos proved they were in a league of their own.
Cain had run through the rankings on his path to a title, smashing the likes of Cheick Kongo, Ben Rothwell, and Antonio Rodrigo Nogueira with his relentless pace, insane cardio for a heavyweight, his stellar wrestling and powerful striking arsenal. After improving his record to a flawless 8-0, Velasquez would receive a title shot opposite the UFC's massive PPV draw Brock Lesnar.
Velasquez would completely embarass the WWE superstar at UFC 121, forcing the inexperienced striker to stand with him and battering his far larger foe in one of the most one-sided beatdowns you'll ever see in a championship fight.
Dos Santos on the other hand had burst onto the scene with a stunning upset knockout of top contender Fabricio Werdum in his UFC debut.
The young Brazilian bomber brought some of the best boxing in the heavyweight division to the table thanks to his extremely heavy and fast hands, his stinging jab, his constant movement and incredible takedown defense.
Junior proceeded to make a name for himself as the most feared striker in the division by demolishing Stefan Struve, Mirko Cro Cop, Gilbert Yvel, Gabriel Gonzaga, Roy Nelson, and Shane Carwin before he finally received his long-awaited title shot against Cain Velasquez late in 2011.
Shortly after the UFC signed a massive new network deal with Fox that was set to become the new home for the UFC in 2012, the UFC and their new network partners wanted to kick off their working relationship by hosting a special event in November before the deal officially started.
Their plan? Put on one of the most anticipated title fights of the year live on basic cable to announce to the world that the UFC was taking over the airwaves.
The partners settled on the massive heavyweight title fight between Cain Velasquez and Junior Dos Santos as the fight to promote, making it the first heavyweight title fight in any combat sport to be broadcast live on free TV in decades. It was a bold strategy given that the fight would have easily pulled a strong buyrate on pay-per-view, but the idea was to use the epic match-up to draw in a massive audience and get them hooked when they witnessed the kind of excitement a great MMA fight can bring.
The extended preliminary card was stacked with exciting fights and broadcast for free on Facebook, with the heavyweight title showdown headlining a special one-hour broadcast on Fox and all of its subsidiaries.
Rather than utilizing the model that had seen them differentiate themselves from boxing and their promotional strategy by putting on a main card full of exciting match-ups, the UFC banked heavily on their heavyweights to deliver, opting for a more boxing-style broadcast focused purely on the top billed fight.
As such their entire one hour broadcast was dedicated solely to Velasquez vs. Dos Santos, expecting an instant classic between arguably the two greatest heavyweights the sport had ever seen at that point.
It ended up being a gigantic miscalculation by the UFC.
After a few warm up fights, the card began to deliver some amazing action, highlighted by Ricardo Lamas' submission of Cub Swanson, Dustin Poirier's D'Arce choke of Pablo Garza in a fun scrap, and a brilliant back-and-forth scrap between Benson Henderson and Clay Guida in a lightweight title eliminator that served as the co-main event.
Unfortunately only the hardcore fans tuned in to the great undercard broadcast on Facebook - the masses instead only tuned in to Fox to watch the UFC's special presentation for their debut on a major network.
After a half-hour of further hyping up the epic clash fans were about to see, over 8.8 million viewers watched as the two heavyweight titans entered the Octagon, by far the largest TV audience the UFC had ever seen for a live event.
But rather than the back-and-forth war everyone was expecting, the fight was over after the first meaningful exchange.
Dos Santos nailed Velasquez with his patented overhand right just a minute into the action, planting the champion before follow up shots put him unconscious.
The entire fight lasted just 64 seconds.
The result wasn't entirely surprising nor was it in any way bad in its own right - Junior was one of the most prolific knockout artists in the division and in a heavyweight fight especially, one shot can end anyone's night early.
The problem was the UFC made a monumental mistake by putting all of their eggs in one basket, a mistake the company had for so long criticized boxing for doing and differentiated itself by avoiding.
The result was that millions of people tuned in for what was essentially an hour long broadcast of pre-fight hype and commentary, all to watch a bout that lasted just 64 seconds.
The biggest irony was that fans had been flabbergasted before the event even occurred as to why the UFC wasn't airing at least the co-main event on TV as well - a lightweight contendership bout between two extremely exciting fighters - and after the event ended, the UFC was surely kicking themselves for not listening.
The penultimate fight between Benson Henderson and Clay Guida was 15-minutes of all-out action, showcasing the entire skillset of modern mixed martial artists as the two traded punches and kicks on the feet and submission attempts and ground and pound on the mat. If the UFC had cut out the commentary and just showcased the two big fights instead, it would have been a home run for the organization and its new partnership.
Instead, their short-sightedness and failure to remember the cardinal rule of heavyweight fights utterly failed in turning the masses on to the sport.
The UFC would begin their partnership in earnest with Fox in 2012, where they would eventually get into a groove and become a solid performer for the network, but never would they reach the viewership numbers they achieved during their initial showcase event.
It was a missed opportunity of epic proportions - although the UFC would continue expanding and gaining popularity to this day, one can't help but wonder how much bigger the sport could be today and how much faster that growth could have been if the UFC hadn't put so much faith on a single heavyweight fight delivering a fight for the ages, or if the first clash between Dos Santos and Velasquez had been more like either of their two rematches.
Instead, it was a misfire that the UFC quickly tried to forget.
1. Royce Gracie vs. Ken Shamrock II
UFC 5, April 7 1995
It really should be no surprise to any longtime fan that the first "superfight" in UFC history ended up topping this list.
It may not have had millions of viewers tuning in to it given it took place while the sport was in its infancy - it didn't capture the eyes of the entire sporting world or generate the kind of mainstream buzz that other fights on this list did - but for fans of the UFC back in the day, this was the fight.
Ken Shamrock was already a recognizable face for combat sports afficianados in the early 90's thanks to his professional wrestling career over in Japan for the UWF (he would later feature in the WWF and various other pro wrestling organizations). Shamrock even had several "MMA" fights on his record prior to the UFC's first event thanks to his participation in Pancrase in Japan, an organization which started by taking pro wrestlers and having them do "shoot" (or real) fights instead of scripted ones.
The musclebound "World's Most Dangerous Man" was a clear favourite in the first UFC tournament just by way of his impressive physique and wrestling background, and he quickly showed his skills by heel hooking Pat Smith in his first fight of the night.
In the semi-finals, Shamrock would face one Royce Gracie, a scrawny Brazilian jiu-jitsu black belt that looked like a nerd about to have his lunch money stolen when he stood across from his hulking opponent.
Royce however had a secret weapon that none of his opponents that night understood - Brazilian jiu-jitsu.
With his brother Rorion Gracie as one of its founders, the UFC was an event created to find out which martial art was superior to all others in true, no-holds-barred combat - the Gracie family believed without a doubt that their family's self-defense system was the clear answer.
They believed so firmly in their art that instead of picking one the family's most proficient athletes and practitioners like Rickson, they chose the gangly Royce, a skinny black belt that weighed 180 pounds soaking wet and was about as physically imposing as a wet paper bag.
The entire foundation of Brazilian jiu-jitsu was to enable someone who was physically inferior to subdue any attacker regardless of size, and thus Royce was chosen to represent the family and prove its effectiveness to the world.
Gracie would show off that ability by easily submitting Art Jimmerson in his first fight that night, a top-15 ranked professional boxer who bizarrely opted to wear a single glove into the cage that night (he said it was to be able to hit hard with his jab while leaving his other hand free in case someone grappled him).
The semi-finals shocked every viewer that night as the massive Shamrock was choked out by Gracie in under a minute, the least imposing figure in the tournament beating the scariest in a matter of seconds.
Gracie would go on to submit kickboxer Gerard Gordeau to win the tournament and showcase his family's martial art to the world, leaving Shamrock to go back to the drawing board. The highly competitive wrestler however was determined to get a rematch and redeem himself.
Royce would go on to dominate the 16-man UFC 2 tournament just the same while Shamrock returned to competition in Japan, returning to compete stateside once more at UFC 3.
The UFC billed the event as the ultimate rematch, with both Royce Gracie and #1 contender Ken Shamrock competing on opposite sides of the bracket in the tournament. The two never made it to the finals however; Gracie managed to submit his massive first opponent in Kimo Leopoldo, but was so exhausted from the match he withdrew from the tournament.
Shamrock made his way to the finals, but after learning that Gracie withdrew and having suffered a knee injury of his own in his semi-final match, Shamrock withdrew as well.
Gracie would come back to win his third tournament at UFC 4 as Shamrock returned to competition overseas, priming a massive rematch at UFC 5.
This time, rather than risking the potential rematch to one of the men losing in the tournament or being unable to continue, the UFC opted to create a "Superfight" championship belt - a non-tournament bout featuring the two early UFC stars in a rematch for the ages.
The turn to a boxing-style main event marked a slow shift away from the tournament format that would slowly transform the sport into what we recognize it as today, and having a proper guaranteed match-up to base promotional material on worked wonders for increasing fan excitement.
The hype was off the charts for UFC fans back in the dark ages, but unfortunately rather than an entertaining fight between the two biggest names in the sport what they received was one of the worst fights in combat sports history.
Determined to prove he was the better grappler, Shamrock took Gracie down early on, but unfortunately he was so wary of being caught in a submission he refused to open himself up for any potential attack - nor would he launch any meaningful assault of his own.
What resulted was half an hour of Shamrock laying on top of Gracie, throwing a few short punches on occasion and doing virtually nothing else for the duration of the "fight".
As the crowd filled the arena with loud boos and nothing happened after 30 minutes of "action", an impromptu five minutes of "overtime" was announced which started after returning the two fighters to their feet.
Ken managed to cut Gracie with a punch before once again finding himself in the same position, with the fight eventually being called at the 36-minute mark and declared a draw given there were no judges at the time.
The agonizingly dull "fight" went on for so long that the UFC was caught completely unprepared for such a situation, the ongoing pay-per-view getting cut off by many broadcasters in the middle of the main fight since it ran past the allotted time slot.
Fortunately that just spared the poor fans from having to see any more of the so-called fight.
The first truly hyped fight in the UFC ended up being arguably the worst bout in UFC history and as such deserves its place atop this list.
The one positive thing to take away from Gracie-Shamrock II is that it really makes you appreciate a dud like Adesanya-Romero or Anderson-Maia, because at least those fights had some funny moments...
Dishonourable Mentions
Hector Lombard vs. Tim Boetsch (UFC 149, July 21 2012)
Tyron Woodley vs. Stephen Thompson II (UFC 209, March 4 2017)
Tito Ortiz vs. Ken Shamrock II (UFC 61, July 8 2006)
Carlos Condit vs. Nick Diaz (UFC 143, February 4 2012)
Jeremy Stephens vs. Yair Rodriguez (UFC on ESPN+ 17, September 21 2019)