If there’s one thing the UFC can credibly claim, it’s that for the better part of the past 25 years, it’s given its fans almost every big fight they could ask for.

Almost.

No, this isn’t another article about dream matchups we wish Uncle Dana had moved heaven and earth to make happen, these are fights that the organization was one step away from making a reality were it not for a few mischievous spoilers.

With UFC 307 on Saturday seemingly designed to set up Alex Pereira and Kayla Harrison for more high-profile bouts, we figured now is a good time to look back at times when the dominoes didn’t fall in the UFC’s favor, and potentially great fights were lost forever in the chaos vortex that is MMA.

Amanda Nunes vs. Kayla Harrison

What happened? Julianna Peña def. Amanda Nunes — UFC 269 (Dec. 11, 2021)

OK, technically this one could still happen, but assuming it doesn’t, our best shot at seeing it was a few years ago.

Amanda Nunes had run through the competition at 145 and 135 pounds, including legendary featherweight champion Cris Cyborg. There wasn’t much left for her to accomplish in the UFC, so eyes searched elsewhere for a viable challenger and lo and behold, there was two-time Olympic judo champion Kayla Harrison tearing it up in the PFL SmartCage. Even better, she was approaching free agency at the end of 2021 and all Nunes had to do was run through Julianna Peña—viewed as little more than a mandatory challenger—to set up a superfight.

Whoops.

Peña submitted Nunes at UFC 269 to cap off a once-in-a-lifetime performance, Harrison reacted to the loss in real time and re-signed with the PFL, and Nunes went on to stomp Peña in the rematch nine months later before retiring in 2023.

Maybe Harrison can still wow us enough to bring “The Lioness” out of her den?

Khabib Nurmagomedov vs. Tony Ferguson

What happened?: Justin Gaethje def. Tony Ferguson — UFC 249 (May 9, 2020)

By the time Justin Gaethje and Tony Ferguson squared off for an interim lightweight title in 2020, most fans had probably given up on the highly touted Ferguson-Khabib Nurmagomedov fight ever happening. But it would have if Ferguson beat Gaethje, for reals this time!

Simply put, Nurmagomedov and Ferguson were the two best lightweights in the world for much of the 2010s (sorry, Conor), and the UFC tried and tried and tried to get them into the cage, to no avail. So much misfortune befell this matchup that at one point we had to write a feature called Timeline of Destruction to recap it all. Dana White even promised they’d fight at UFC 249, which went about as well as most of his other promises.

Sure enough, the COVID-19 pandemic prevented Nurmagomedov from traveling, so Gaethje stepped in as his replacement and thoroughly drubbed Ferguson. This wasn’t just the final nail in the coffin for Tony-Khabib, it was the start of Ferguson’s seemingly interminable losing streak that goes on to this day.

Randy Couture vs. Mirko Cro Cop

What happened?: Gabriel Gonzaga def. Mirko Cro Cop — UFC 70 (April 21, 2007)

The original heartbreaker.

With each passing day, it becomes more difficult to explain to newer fans just how tantalizing it was to imagine the stars of PRIDE crossing over to battle the UFC’s best in the 2000s. And one of the most intriguing possible matchups was PRIDE’s heavyweight knockout machine Mirko Cro Cop going toe-to-toe with “Captain America” himself, Randy Couture.

Cro Cop’s path to a title shot went through Gabriel Gonzaga, a talented but untested contender in just his ninth pro bout. Everyone expected Cro Cop to kick Gonzaga to the curb and set his sights on the UFC heavyweight title.

Someone got kicked, alright.

In one of the best knockouts ever, Gonzaga head-kicked the bejeezus out of a man known for head kicks, and staked his own claim to Couture’s title, albeit an unsuccessful one. Eight years later, Cro Cop earned a measure of revenge over Gonzaga with a third-round TKO in their rematch, but the Couture fight remained the one that got away.

Rafael dos Anjos vs. Conor McGregor

What happened?: Nate Diaz def. Conor McGregor — UFC 196 (March 5, 2016)

We all remember the broken foot that forced then-lightweight champion Rafael dos Anjos out of UFC 196, which set up the 2016 Conor McGregor-Nate Diaz feud that sent combat sports hurtling uncontrollably into the chortling void that it is today. But could the timeline have corrected itself if McGregor had just beaten Diaz in their first fight?

Keep in mind, dos Anjos was later scheduled to defend his title against Eddie Alvarez at a UFC Fight Night on July 7, with McGregor rematching Diaz at UFC 200 on July 9. It’s safe to say that dos Anjos vs. McGregor would have headlined UFC 200 were it not for McGregor demanding his chance to avenge the Diaz loss (in reality, McGregor vs. Diaz 2 landed on UFC 202, for reasons that are hardly worth rehashing).

What we ended up getting was dos Anjos dropping the belt to Alvarez, Alvarez dropping the belt to McGregor, McGregor booking a boxing match against Floyd Mayweather Jr., a bunch more weirdness after that and now Jake Paul is boxing Mike Tyson next month.

Michael Bisping vs. Yoel Romero

What happened?: Robert Whittaker def. Yoel Romero — UFC 213 (July 8, 2017) and Georges St-Pierre def. Michael Bisping — UFC 217 (Nov. 4, 2017)

Michael Bisping became middleweight champion with a shocking first-round knockout of Luke Rockhold (on short-notice, no less) and then proceeded to defend his title against a 46-year-old Dan Henderson. The wonky matchmaking could be forgiven due to Henderson’s popularity and the history between the two, but after Bisping escaped with a narrow decision win, fans were eager to see him take on a hungry challenger like Gegard Mousasi, Robert Whittaker, or Yoel Romero.

It was Romero that whet the appetite the most as the Cuban juggernaut built up a healthy rivalry with the champ, capped off by this unforgettable moment:

Unfortunately, a lingering knee injury kept Bisping out for months after the Henderson fight, so Whittaker and Romero were booked to battle for an interim belt at UFC 213. Whittaker beat Romero, and then Bisping lost at UFC 217 to a returning Georges St-Pierre, who likely had no intention of sticking around after capturing his second UFC belt.

That was the disappointing end of Bisping vs. Romero, and to this day there are still fans sour it never happened because they’re convinced Romero would have mashed Bisping into British pudding.

Wait, I think I hear one of those fans now.

Jed Meshew: DASTARDLY, SKULLDUGGEROUS, CHICANERY!!!

One of the great travesties in modern MMA is that Yoel Romero will never be recognized as even an interim champion. This is a man who, for at least a couple of years, was the best middleweight alive and wasn’t given his chance to prove it. When he finally did, the judges robbed him (I believe Romero beat Whittaker the first time around in a very close fight, but there is no debate he deserved to win the rematch at UFC 225).

In a world where MMA was even marginally meritocratic, Bisping wouldn’t have been allowed to do his backyard nonsense of calling his own title challengers, and I truly cannot imagine a worse fight for “The Count” than Romero would have been. They’d still be mopping up the pieces today.

Aljamain Sterling vs. Jose Aldo

What happened?: Merab Dvalishvili def. Jose Aldo — UFC 278 (Aug. 20, 2022)

It’s a stretch to say that Aljamain Sterling and Jose Aldo were on a collision course, but it’s not a stretch at all to say that fight should have happened instead of Sterling defending his bantamweight title against a one-shouldered T.J. Dillashaw. A one-shouldered T.J. Dillashaw coming off of a knee injury, a controversial decision win over Cory Sandhagen, and a drug suspension.

I’m still so, so, so angry about this.

Aldo, one of the five greatest fighters of all time, was right there. The featherweight GOAT was coming off of three straight wins over ranked 135ers and deserved one more chance to become UFC champion. For whatever reason, the matchmakers felt that they just had to do Sterling vs. Dillashaw (how’d that one turn out, guys?), so that was booked for UFC 280 and Aldo had to fight Sterling’s buddy Merab Dvalishvili at UFC 278.

Dvalishvili won a dreary decision, a result so uninspiring that Aldo said “f*ck it I’m going to take a couple of boxing matches” before returning to the UFC earlier this year.

Jon Jones vs. Alex Pereira or Tom Aspinall

What happened?: Stipe Miocic def. Jon Jones – UFC 309 (Nov. 16, 2024)

Oops, sorry that one hasn’t happened yet. My bad.

Honorable mentions:

Chuck Liddell vs. Wanderlei Silva (in PRIDE)

This one doesn’t count because we eventually got to see “The Iceman” and “The Axe Murderer” throw down at UFC 79, and it totally ruled, but there was an insane amount of buzz when these two first entered each other’s orbits in 2003.

PRIDE set up an eight-man tournament to manufacture a Chuck Liddell vs. Wanderlei Silva final, but Rampage Jackson had other plans. He knocked Liddell out in the semifinals to set up an epic rivalry with Silva and also scared then-UFC commissioner Dana White from venturing to other promotions with his fighters.

Frankie Edgar vs. Anthony Pettis

UFC lightweight champion Frankie Edgar vs. WEC lightweight champion Anthony Pettis wasn’t exactly the most hyped matchup of 2010. Still, it feels weird these two lifers never fought after it seemed like a guarantee they would.

Pettis was hot off of a Fight of the Year-win over Benson Henderson, capped off by the “Showtime Kick” that had Pettis on the cusp of superstardom. As luck would have it, his shot at UFC gold would have to wait as Edgar and Gray Maynard fought to a draw at UFC 125 and their rematch didn’t take place until UFC 136. Pettis couldn’t keep waiting, so he booked a fight with veteran Clay Guida.

Guida wrestled Pettis into oblivion, forcing Pettis to battle his way back to contention. Ironically, Henderson—the man Pettis beat in the last-ever WEC event—went on to defeat Edgar for the title instead. Pettis eventually defeated his rival again to become UFC champion, but Edgar had dropped to featherweight by then so this intriguing pairing was gone for good.

Ronda Rousey vs. Cris Cyborg

Unquestionably one of the most talked-about fights that never happened, Ronda Rousey vs. Cris Cyborg doesn’t make the cut due to the fact that you can’t pin down one result to change that would have sealed the deal.

It always felt like so much bluster between these two, with Rousey challenging Cyborg to make an impossible cut down to 135 pounds and Cyborg attempting to coax Rousey into a catchweight bout that Rousey had no incentive to take. Maybe you can blame Holly Holm for derailing Rousey at UFC 193, but Cyborg was yet to make her UFC debut and Rousey wasn’t waiting for her even if she had escaped Holm.

Jon Jones vs. Anthony Johnson

Once upon a time, Jon Jones was supposed to fight Anthony Johnson at UFC 187. A month before that May 2015 event, the light heavyweight champion was involved in a hit-and-run where he crashed into a car containing a pregnant woman, and was subsequently stripped of his title and suspended. That resulted in Johnson fighting for a vacant title at UFC 187, where he came up short.

So why doesn’t this make the list? Because the fighter Johnson lost to was Daniel Cormier.

The Jones-Cormier rivalry was always going to define that era of the 205-pound division, so while it’s fun to imagine how Jones would have fared against Johnson’s fearsome punching power, fans ended up getting the fight they really wanted anyway.