5 of the best booked fights we never got to see

The fight game is notoriously unforgiving, with every triumphant moment inevitably followed by an equally daunting low point. This can come in the form of a crushing loss, or even worse, the sudden and unforeseen withdrawal of a scheduled opponent. While it may seem counterintuitive, an opponent pulling out of a fight is actually worse than losing in the cage. Consider this: you've spent six to eight weeks, or even longer, training specifically for an opponent's style and technique. 

In an alternate universe, pivotal MMA fights took place, fundamentally altering the trajectory of the sport. These matchups would have sent shockwaves through the world of mixed martial arts, forever changing the course of history. But for one reason or another, it was not meant to be. Either attempts to rebook the scheduled bout remained cursed, short-notice fighters stepped up to the plate, or plans for the division changed entirely. 

Although we can't turn back the clock, fans were left to lament missing out on five compelling fights that could have been among the most iconic and thrilling in mixed martial arts history.

5. Brock Lesnar vs. Junior Dos Santos

The UFC's heavyweight division languished in a state of uncertainty and disarray throughout the latter half of the 2000s and into the early 2010s. Though not entirely his fault, one of the fighters who influenced the heavyweight division to fall into limbo was Brock Lesnar. The former WWE star quickly became a cash cow for the UFC, where they booked him into a questionable championship bout with Randy Couture, which Lesnar subsequently won. Lesnar proved his doubters wrong with gutsy performances against Frank Mir in a heated grudge match, and a battle of titans with Shane Carwin. However, Lesnar’s UFC heavyweight tenure was not without its roadblocks, as the Minnesota State product battled a fierce battle with diverticulitis (a digestive disease that affects the large intestine). 

It soon became a war to save Lesnar’s life rather than rallying him back in the Octagon. As much time as it took of Lesnar’s UFC career, he was able to come back and defend his title, this time against a rising young contender in Cain Velasquez. Velasquez proved too much for the megastar Brock as he finished him by TKO in their UFC Heavyweight title main event at UFC 121. 

Looking to bounce back into the win column, Lesnar was matched up as an opposing coach on The Ultimate Fighter season 13, against blossoming heavyweight standout Junior Dos Santos. The two were set to battle in a main event slot at UFC 131, but Lesnar’s lingering diverticulitis proved detrimental once again, as he was forced to withdraw from the scheduled fight a month out from the PPV. Filling in place of Lesnar was his ex-adversary Shane Carwin, who was later handed a dominant decision loss courtesy of “Cigano”.

Lesnar vs. Dos Santos was a super intriguing matchup of styles in the heavyweight division at the time. JDS was a lethal striker, with some of the best boxing in the UFC. Lesnar, of course, was an accomplished collegiate wrestler with heavy ground and pound. Brock later returned to fight Alistair Overeem at UFC 141, who quickly dispatched the behemoth with a vicious body kick, subsequently departing the UFC for a WWE return. The recurring illnesses faced by Lesnar can ultimately be attributed to his fall from grace in MMA, but you can’t help wondering how a JDS vs. Brock matchup would’ve played out. 

4. Leon Edwards vs. Khamzat Chimaev

As is the case with many of these matchups, the fighters scheduled to be involved went down separate paths in their UFC journeys. Birmingham’s Leon “Rocky” Edwards had quickly made a name for himself in the UFC’s welterweight division, riding an 8-fight unbeaten streak. It seemed Edwards was tabbed to be next in line for champion Kamaru Usman at the time, but the UFC wanted him to first get passed a rising prospect out of Sweden. 

Khamzat Chimaev bursted onto the UFC scene during its pandemic-era “Fight Island” days. “The Wolf” pulled off two wins in a ten-day period, cementing himself in the record books for quickest UFC turnaround wins of the modern era. Capped off with a middleweight demolition of veteran Gerald Meerschaert, it seemed like Chimaev was set on conquering both the welterweight and middleweight divisions. However, his next scheduled bout was set to be a title eliminator of sorts with Leon Edwards back down at 170. This was Khamzat’s golden opportunity to skip a list of contenders and defeat one of the welterweight division’s absolute best in “Rocky” Edwards. 

Leon could stick it to the UFC, who didn’t seem keen on granting him a title opportunity, and make a name off their handpicked, seemingly unstoppable star in Chimaev. The two were set to main event a UFC Fight Night card in December 2020, but both Chimaev and Edwards came down with COVID-19, which cancelled the bout. The UFC were set on running the scheduled matchup back for a Fight Night card in March 2021, but once again Chimaev fell ill to COVID-19 and Leon instead fought Belal Muhammad to a no-contest. 

Fast forward to the present day, and constant pullouts continue to be the crippling component to Khamzat Chimaev’s UFC career remaining stagnant. He’s since moved up to 185, setting his sights on that division’s title picture, but “The Wolf” has never been able to make his scheduled bouts. Leon Edwards on the other hand has since become the UFC welterweight king, pulling off a miraculous round 5 comeback over Kamaru Usman, a subsequent victory in their rematch, and a title defense over loudmouth Colby Covington. The state of 170 could look a lot different today had Leon Edwards and Khamzat Chimaev locked horns. Their dynamic and opposite styles would’ve been a treat to see go toe-to-toe, and one can only wonder who could’ve come out on top. It had all the makings for a compelling and competitive show. 

3. Jon Jones vs. Dan Henderson

This is the one fight on our list where a matchup falling through resulted in an entire PPV card to be scrapped. Enter the UFC 151 fiasco that was supposed to be Jon Jones vs. Dan Henderson.  

No young champion had broken out in such dominant fashion as light heavyweight king Jonny “Bones” Jones. Stepping in on short notice for an injured Rashad Evans (a close teammate at the time), Jones made light work of titleholder Mauricio “Shogun” Rua, to claim the 205 crown and become the youngest UFC champion in history. He would go on to defeat former champions, Quinton “Rampage” Jackson, and Lyoto Machida, in respectively impressive submission victories. For his third scheduled title defence, Jones was tabbed for a matchup with longtime MMA veteran and world-renowned cross-organization champion, Dan “Hendo” Henderson, who was riding off a victory in a 2011 Fight of the Year with ex-champ Shogun Rua. 

Though one of the fight game’s oldest competitors, Hendo proved he still had a lot in the tank and recently showed he was still championship material, claiming Strikeforce’s light heavyweight title in March 2011, ironically the same month Jon Jones claimed his UFC title. The bout was set to headline UFC 151 and had all the makings for an interesting stylistic clash. Jones showed to be skillful in every area of mixed martial arts, but it’s wrestling that serves as his fighting basis. While Dan Henderson was a praised collegiate and Olympic wrestler, who developed heavy hands in his MMA career with a patented “H-Bomb” shot that could put anyone’s lights out. 

The age and reach difference aside, you couldn’t count out old man Hendo from posing a serious threat to his younger champion adversary in Jon Jones. Unfortunately, Hendo would pull out of the matchup citing a knee injury, and the UFC scrambled to book a new, short notice main event for their UFC 151 PPV. They quickly shifted attention to middleweight contender Chael Sonnen, who Jones ultimately declined to fight as he believed the pull out was an inside job and that Sonnen did not deserve a title shot. 

The UFC ultimately decided to cancel the card entirely, as Jones was rescheduled for a UFC 152 headlining spot against Vitor Belfort, while the Sonnen beef eventually grew into a title shot vs. Jones which took place at UFC 159. Henderson never found himself in the 205 title hunt again after the Jones bout fell through, as he dropped three fights in a row following the UFC 151 debacle. 

2. Dustin Poirier vs. Nate Diaz

“The Diamond” and the 209’s very own. This fight had all the makings to be an all-out war. Dustin Poirier and Nate Diaz are some of the sport’s most celebrated stars, who catapulted their MMA careers through heated rivalries with polarizing megastar Conor McGregor. However in the Fall of 2018, when this fight was originally planned to take place, both men were on two completely different trajectories. Poirier had come off a dominant string of victories at 155, finishing former champ Anthony Pettis, top contender Justin Gaethje, and another ex-155 kingpin in Eddie Alvarez. The sky was the limit for Dustin Poirier, who was itching very close to a title shot, but instead he rerouted plans to one of the sport’s top bad boys. 

Nate Diaz hadn’t fought in over two years, with his last fight coming at UFC 202 in a memorable rematch with Conor McGregor. Diaz had the opportunity to jump the gun and fight off the lightweight division’s top contenders in a co-main event slot at UFC 230. With the championship set to be decided at UFC 229 between Khabib and Conor, the winner of Poirier-Diaz could’ve easily been next in line for the next title shot. 

Alas, the exciting pairing were not meant to tango, as Poirier fell through due to a hip injury which resulted in Nate Diaz being pulled off the card entirely. Instead, Diaz would return to the Octagon almost a full year later, at UFC 241 in a winning effort over Anthony Pettis. While Dustin Poirier would be granted an interim title opportunity against featherweight champ Max Holloway, who “The Diamond” successfully defeated. Considering both of these men’s styles to stand and trade, while also possessing slick jiu-jitsu skills, one can only ponder at the aura that could’ve been this historic fight. 

Attempts to reschedule the bout were never made, and the two fighters each branched off into different plot lines in their respective careers. But, it really hurts looking back, as fans could’ve been treated to a “BMF” worthy fight before that moniker was even coined. 

1. Khabib Nurmagomedov vs. Tony Ferguson

This is the absolute holy grail of cancelled, what-if, MMA lore. Enter the cursed world that is Khabib Nurmagomedov vs. Tony Ferguson. These two lightweights were scheduled to do battle not once, not twice, not three, not even four times, but a whopping five attempts were made to see Nurmagomedov vs. Ferguson. 

December 2015, April 2016, March 2017, April 2018, and April 2020. That’s every single period in which fight fans were so close to seeing two of 155’s best fighters finally settle the score. Out of all the scheduled fights to fall through, it seemed like their UFC 249 main event bout for April 2020 was going to finally be the one. It’s not common to have two fighters in the same division who are both on dominant 12-fight win streaks. It didn’t seem like any untimely injuries were on the horizon, and the MMA community were simply counting down the days before Khabib-Tony was set in stone. 

And then, the whole world turned upside down. The COVID-19 pandemic prevented Khabib from being able to travel, and Tony Ferguson instead fought top contender Justin Gaethje in an interim title fight, which “El Cucuy” lost in a surprising, mercy-like stoppage. When Khabib did return, he settled undisputed lightweight champion status by defeating Gaethje, while Ferguson spiraled down what is now a 7-fight losing streak. 

When these two men were at their absolute best, no one else at 155 could state their case as the division’s top one and two fighters. They were also among some of the top pound-for-pound fighters in the UFC, and it’s an absolute travesty that fight fans were never treated to a successful matchup. Sure, many can point to Ferguson’s downfall now as proof he would’ve fallen victim to Khabib, but keep in mind who prime “El Cucuy” was. We’re saying both at the top of their games, peak prime, you can’t really say for sure who would’ve won. Tony was a madman who could endure any adversity at one point in his career, while Khabib possessed an aura that made him seem like an impossible puzzle to solve. It's such a shame.