Was Tony Ferguson better than Khabib Nurmagomedov? That was the question on everyone’s mind back then. The UFC was just as eager to find out who would come out on top. Between 2015 and 2020, the promotion attempted to book the fight five different times, but every attempt collapsed under bizarre twists of fate—injuries, illnesses, even global lockdowns. As a result, this blockbuster matchup never materialized, earning its reputation as the most “cursed” fight in UFC history. Though in 2020, the chances looked more promising.

The world was locked down due to the COVID-19 pandemic, yet the UFC continued to produce fights. Finally, Khabib vs. Tony was projected for UFC 249 on April 18, 2020. However, with Khabib stuck in Dagestan because of travel restrictions, the fight fell apart once again. Instead, ‘El Cucuy’ was set to face Justin Gaethje on the same card. To make matters even worse, the entire event was uprooted from California and shifted to Jacksonville, Florida, with a new date of May 9. That night turned into a nightmare for Tony Ferguson, as Gaethje handed him a brutal TKO defeat. Still, fans couldn’t help but wonder, what if Khabib had fought Ferguson that night?   

Who really wins: Khabib Nurmagomedov or Tony Ferguson?  

Now, let’s imagine Khabib actually made it to UFC 249 and was set to face Tony Ferguson. That fight would have driven the most audience interaction since the Dagestani clashed with Conor McGregor. And honestly, it would’ve been even more interesting, since Ferguson had far more tools to give the undefeated phenom the toughest challenge of his career.

‘The Eagle’ was known for pressuring opponents with his relentless grappling, but what made him truly dangerous was how he mixed in his judo throws and then used his entire body weight to smother and control. On top of that, Khabib had an incredible ability to find submissions. His striking, though unorthodox, was effective. He often faked a takedown to land an overhand right that caught many strikers off guard. In short, he combined awkward but effective striking with world-class grappling, a mix that would’ve been incredibly difficult for Ferguson to handle.  

However, ‘El Cucuy’ also had some slick hands back in his prime. His elbows were among the sharpest in the game, cutting open fighters like Anthony Pettis and Donald Cerrone. Ferguson would have absolutely used that weapon in the fight. But his scrambles would’ve been his most valuable tool for getting off the mat. McGregor had Gaethje on his radar too, which made Ferguson’s fight doubly significant. Khabib likely would have switched to grappling after landing a few blows. And that’s where things would’ve gotten very interesting. 

As we saw in Ferguson’s clashes against Charles Oliveira and Beneil Dariush. Relentless pressure grappling can become overwhelming for him. In both fights, the Californian struggled to get back to his feet. By that logic, Khabib would have been an even tougher grappler to handle. Still, does that mean ‘El Cucuy’ couldn’t catch him? Of course not. But the majority of predictions would still favor the Dagestani champ because of the aforementioned reasons. And if this fight had actually happened, the winner might have gone on to face Conor McGregor as well. 

Would Conor McGregor have faced ‘The Eagle’ once again?

Conor McGregor was fresh off his victory against Donald Cerrone at UFC 246 when Ferguson and Gaethje were set to battle at UFC 249. According to an article by Ariel Helwani on ESPN, ‘The Notorious One’s manager, Audie Attar, at Paradigm Sports, revealed that McGregor wasn’t very interested in fighting inside an empty venue with no crowd to cheer him on. Instead, he decided to wait for July, when the UFC planned to bring fans back amidst the COVID-19 pandemic.

However, in the same article, Attar also claimed that McGregor planned to closely watch the UFC 249 main event. So, he was definitely invested in the outcome of that fight. He also wanted to fight Gaethje as well. So, needless to say, if Khabib and Tony had actually squared off in Jacksonville, Dana White would have done everything possible to convince the undefeated Dagestani to accept a rematch against the Irishman.

Still, for ‘The Eagle,’ the chapter on McGregor was already closed. He had settled the grudge match at UFC 229 with a dominant victory. That’s why it wouldn’t be a stretch to say that Khabib might have rejected the offer, even if he had beaten Ferguson. But the story would have been very different if ‘El Cucuy’ had actually pulled off the win.  

What if ‘El Cucuy’ actually pulled it off?  

It was always uncertain whether Khabib would ever agree to a mega-rematch with Conor McGregor to shatter pay-per-view records again. But if Tony Ferguson had somehow managed to defeat the Dagestani champ, he would have been absolutely ready to fight ‘The Notorious One’ in a heartbeat. The two had been trading verbal blows for a long time, and it would’ve been a perfect opportunity for the UFC to capitalize on another blockbuster fight.

But since we’re now discussing Ferguson vs. McGregor, another question arises: wouldn’t ‘The Eagle’ have demanded an immediate rematch? Most likely, yes. However, Dana White would’ve had two big options if ‘El Cucuy’ had beaten Khabib. He could match Ferguson up with Conor, while Khabib recovered from his first-ever loss. And if McGregor beat Ferguson, the rematch with the Dagestani was right there on the table. Maybe it wouldn’t have carried the same magnitude, but it still would’ve been huge.

If Ferguson had beaten McGregor, the next logical step would’ve been a showdown with Khabib. Pretty crazy scenario. But that’s most likely what would have happened if Khabib Nurmagomedov and Tony Ferguson had finally fought at UFC 249. In another timeline, the outcomes could’ve been slightly different, or drastically so.

With that being said, Ferguson vs. Khabib remains one of the most popular “what ifs” in MMA history. Right up there with what if Khabib never retired? So, what do you think about the UFC’s most cursed fight? Got better ideas about how it could have played out? Share your thoughts in the comments below.