The 7 Biggest UFC Fights That Never Happened
MMA is a fickle mistress. More than any other sport, it giveth and taketh away seemingly on a whim. Fights are booked and unbooked based on injuries or drug test failures or pretty much all the things that have happened to Jon Jones. There have just been so many times and reasons to be excited—and so many times and reasons that such excitement was over before it reached its proper crescendo.
The end result for fans is that they’re often left wanting for fights that get pushed into the distance indefinitely or canceled entirely. Maybe they’re never booked in the first place, and those fans find themselves complaining that matchmakers could not get two athletes in the cage together to throw down.
It’s happened countless times, even if many of the matchups that fans and pundits craved were blocked by pesky things such as fighter contracts with other organizations or the limits of their very imaginations. As the UFC has expanded and grown in its share of the MMA market, it seems to be happening less often, but there are plenty of fights have slipped through the cracks over the years.
Making the biggest fights between the biggest names is the best outcome for everyone: Fans see what they want, the UFC makes a fortune, and fighters increase their income and exposure—it’s the classic example of a rising tide lifting all boats. And still, so many have been lost.
This list looks at seven of the biggest, most influential fights that we’ve all missed out on over the years.
Randy Couture vs. Mirko Cro Cop
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In 2007, there was simply nothing bigger in the MMA world than the idea of Randy Couture fighting Mirko "Cro Cop" Filipovic. Couture had left the world slack-jawed with his destruction of Tim Sylvia and against-all-odds reclaiming of the UFC heavyweight title, and the UFC had just purchased Pride on the way to bringing its biggest stars into the promotion.
It was finally time to see how the athletes of the two most important, influential fight organizations in the history of the sport would stack up against one another.
Everyone—everyone—wanted to see how Cro Cop, the biggest, scariest heavyweight outside of the UFC (besides a certain Russian Emperor, who we’ll deal with momentarily), would stack up against Captain America. It was the ultimate striker vs. grappler matchup, with Cro Cop’s lethal left head kick clashing with Couture’s durable, bullying style. Whoever would impose that for which they were famous would come out on top.
And we never got to see it.
Cro Cop fought Gabriel Gonzaga in an obvious tuneup fight at UFC 70, but there was something missing from the start. He looked tepid and uncomfortable as he half-heartedly stalked the Brazilian, and he eventually didn’t make it out of the first round. Gonzaga hit him with, of all things, a savage head kick and walked away as the shocking winner.
He’d go on to convincingly lose to Couture at UFC 74 a few months later, while Cro Cop floundered for years as a UFC heavyweight, never coming close to the title or any fight with The Natural.
Fedor Emelianenko vs. Randy Couture
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As mentioned previously, the true ruler of the heavyweight world in the 2000s was Fedor Emelianenko. A proper candidate in the discussion for not only the best heavyweight but the best mixed martial artist to ever play the game, the native of Stary Oskol made his bones in Pride with a run of legendary performances that buoyed an unbeaten streak a decade long.
When a character of such import is out there and you’re the biggest name on the other side of the fence, you’re going to want to test yourself against him, and that was very much the case for Couture. Since he was a multi-time UFC champion across two weight classes, everyone following the sport knew that they were watching an iconic career unfold every time he took to the cage. Ever the opportunist and competitive purist, Couture wanted to capitalize on his and Fedor's stock in hopes of finding out who was the best heavyweight on the planet.
And again, much like the Cro Cop fight, it never happened. Granted, this one got a little closer.
There was a lengthy dispute between Couture and the UFC over his contract, one that actually got Couture so close to his proverbial unicorn fight that he showed up on an Affliction broadcast and went nose-to-nose with Emelianenko in a surreal faceoff. Unfortunately for those who wanted to see the fight, Couture’s legal challenge of his UFC deal didn’t pass muster, and he was never able to escape the UFC's clutches long enough to get his knuckles on The Last Emperor.
It’s a sore point to this day that the two never came any closer than that staredown, save for sharing a video game cover at one point—so much so that Couture, now an actor in his 50s, is still asked about it and doesn’t dismiss it outright when it comes up.
For him and for fans, it’s the ultimate one that got away.
Fedor Emelianenko vs. Brock Lesnar
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Given that he’s never fought in the UFC and has been in off-and-on negotiations with Dana White for seemingly a lifetime, Emelianenko is almost a white rabbit in the sport: If he has have ever taken the plunge into MMA’s main promotion, the discoveries you would have unearthed by following him would be almost too much to handle.
The definitive discovery: Would he, in his prime, have beaten the immovable Brock Lesnar?
In 2009, Lesnar was one of the scary mixed martial artists alive. He was as inhuman as he was inhumane, a raw athletic freak who seemed to show that he enjoyed inflicting pain on people with every fight he took in his young career. At UFC 100 against Frank Mir, he delivered one of the most malicious beatings the sport had ever seen and left the cage frothing at the mouth and badmouthing sponsors.
He was an animal, one who seemed to be coming into his fistic peak at a time when the UFC’s heavyweight division needed a replacement for Couture—whom Lesnar had actually beaten to become champion in late 2008.
Seemingly no one could stop him.
Or could they?
At the same time, Emelianenko was floating around outside the UFC still plying his trade, racking up convincing wins against decent opponents and showing no signs of decline. He had the exact tools to beat Lesnar—a good bottom game, bricks in his hands and a stoic fearlessness that could only come from 10 years traipsing through the nightmares of every heavyweight on the planet.
There’s no way to know how the fight would have played out, but it was big enough for the UFC to pursue it as a headliner in Cowboys Stadium, and it even bubbled back to the surface this year when both men made surprising returns to MMA.
Some interests die hard, and the unconsummated theoretical Fedor vs. Lesnar tussle is one of them.
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Georges St-Pierre vs. Anderson Silva
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Looking back on it, with Georges St-Pierre being more or less forced into retirement and Anderson Silva much closer to the end of his career than the beginning, it feels strange that the two best to ever do it never met when they were ruling their respective divisions. They were destroying competition a mere 15 pounds apart for so long that people had taken their reigns for granted. The question of a fight between them was put forth on a few occasions, but it just never came to be.
The narrative people probably remember is that St-Pierre wasn’t keen to go to middleweight for a superfight and wouldn’t go beyond a catchweight (if he was even interested in that much). Still, with time and space to consider how things were then, Silva didn’t seem crazy about the fight either. He had competed at 167 pounds in the past and wouldn’t budge on weight whenever a GSP fight came up.
Overall, it really felt like a fight that neither guy wanted and both would work harder to avoid than to put together.
As MMA matures and grows, these two men are going to be remembered as the first great stars of the sport. They were athletes and lifetime martial artists who trained like professionals; they had major sponsorships, and people wanted to see them and be seen with them. As that perspective becomes more accepted, the question that’s likely to follow is: How did they never fight each other?
It’s tough to say for sure, but it’s disappointing they never did.
Dan Henderson vs. Jon Jones
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2012 wasn’t a great year for the UFC. The promotion was in a bizarre situation where it was rapidly expanding to meet the growing need for its product as a result of its television deal with Fox but doing so without the talent to meet that need. There were too many cards and too few fighters to go around, which caused some unforeseen and often unprecedented happenings.
The peak of the chaos came at the end of the summer when Dan Henderson was forced out of a light heavyweight title fight with Jon Jones at UFC 151. Upon disclosing his injury to the UFC, there was a fevered scurry to replace him, and although Chael Sonnen inserted himself into the fray and challenged Jones, the champ did the unthinkable: He refused.
The event was canceled.
Without Henderson in the mix, Jones didn’t want to take on a drastically different fighter on such short notice and simply dug his heels in. No amount of fan frustration or Dana White bullying would change his mind, and Jones eventually found his way onto the UFC 152 card in a defense against Vitor Belfort instead.
The end result of one of the crazier three-week stretches in UFC history was that Henderson, to his admitted regret, never did fight Jones. Bones successfully defended against Belfort and then beat Sonnen a few months later as well.
Still, Henderson vs. Jones was lost forever, and UFC 151 remains the only formally canceled event during the lifetime of the UFC.
Jose Aldo vs. Anthony Pettis
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This fight was alive, then dead, then alive again, and now it looks dead again. Such is the way it goes in MMA, where even the most appealing concepts are sometimes fleeting.
Back in 2012, Aldo was featherweight champion, and Pettis was among the hottest 155-pound commodities going. They began to circle each other in the midst of a fairly muddled lightweight title picture that had left Benson Henderson fighting TJ Grant and Pettis without a dance partner at all.
Aldo had long pondered a move north from his 145-pound class and saw this as a perfect chance. If he beat Pettis, even in a featherweight fight, he would usurp him in the queue for a crack at lightweight gold.
Both men seemed keen on the bout, so much so that it was booked for UFC 163 and fully promoted as the can’t-miss proposition it was—complete with intense beachfront staredowns. The deal was that Pettis would fight for the featherweight title and Aldo would defend, but if Aldo won, he would get a shot at the lightweight title against the winner of Henderson vs. Grant, which was booked for UFC 164.
What followed was one of the strangest unravelings of a fight to befall the UFC: Grant pulled out of UFC 164 with a concussion that still has him sidelined over four years later. Pettis also pulled out of the Aldo fight, citing a knee injury that would prevent him from making UFC 163. Then, seemingly overnight, the UFC rebooked Pettis to replace Grant given that the fight was in his hometown, leaving Aldo out in the cold and Pettis to eventually become lightweight champion.
The whole process robbed the sport of two of the prettier strikers in the game coming together to produce certain violence—an offering so interesting that people still ponder it today when discussing the best fights the sport never quite got to see.
Conor McGregor vs. Rafael Dos Anjos
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At this point in his UFC career you could probably put together a list of fights McGregor has missed out on—Andy Ogle, Cole Miller and a few against Jose Aldo—but perhaps the biggest, for a few reasons, was his chance at Rafael Dos Anjos.
Heading into UFC 196, McGregor was lined up for a chance at lightweight champion Dos Anjos and some associated history. If he won the fight, he’d become the first man in the UFC to simultaneously hold titles in two weight classes. Dos Anjos pulled out, though, leaving Nate Diaz to replace him and start one of the wildest six-month feuds in UFC history by stunning and stopping McGregor in the replacement main event.
The fallout reverberated through the year and continues to this day, as McGregor and Diaz both collected massive purses at UFC 196 and even bigger scores in their rematch at UFC 202. McGregor continues to hold his featherweight title while focusing on pursuits outside the division to the frustration of his cohorts and the obvious delight of his fans. He’ll fight Eddie Alvarez, who eventually dethroned Dos Anjos upon his return, in November at UFC 205 in the first UFC event in New York.
Even so, this was a fight that people wanted to see unfold. Could McGregor move up in weight and handle a brawny former welterweight with superior wrestling and vicious stand-up? Would Dos Anjos, something of a late bloomer who was unheralded right up to the final seconds of his title reign, end the hype of the sport’s most boisterous star?
It’s a fight that could still happen one day but never with the anticipation and excitement it had leading into UFC 196. That’s lost forever.
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