UFC Best Ever: Biggest UFC "What If" Fights We Never Saw

Zak Drapeau
2 minutes ago
5 min read

by Zak Drapeau

Sportz Nation - 2/25/2026

Photo Courtesy of @khabib_nurmagomedov/ Instagram

First thing's first, this is a list about how much we wanted to see the fight, NOT about how great the fight would've been.

So much get's put into the sport of MMA that we forget that the UFC is foremost a spectator sport. While we appreciate the purity of the #1 contender facing the long-anointed champion, we also want to see the fights we want to see.

There's something different about watching walkouts and fights between huge celebrities that bring us to the point where they stare down in the cage before they get it on.

While none of the fights in the below list happened, they all peaked our interest and captivated our attention for at least some time, while some of them were anticipated for over 5 years.

Without further ado, let's get on to the biggest WHAT IF's, in UFC History.

10. Ronda Rousey

vs Cris Cyborg

This is the lone female fight on the list and was all the rage back in 2016, when the greatest woman combat athlete we had ever seen to that point Ronda Rousey was at her peak, and Cris Cyborg was the greatest woman NOT in the UFC yet. 6 months before Cyborg eventually made it to the Octagon, Rousey had just been slept by Holly Holm and from then on, Amanda Nunes took over and we never got to see this dream fight from the mid-2010's.

9. Khabib Nurmagomedov

vs Tony Ferguson

This fight was famously booked and cancelled 5 different times between 2015 and 2020 when both of these men were undefeated and part of the elite group of Lightweights during this time. Eventually centered around the Lightweight title around Khabib's waist before a 2020 beatdown by Justin Gaethje cut off any hopes of Tony staying at the top. For years, this fight was to find the best Lightweight on the planet before we eventually figured out that it was always Khabib.

8. Fedor Emelianenko

vs Randy Couture

I have to bring us all the way back to 2008 for this one so strap in. Fedor is recognized as one of, if not the greatest Heavyweight Mixed-Martial Artists of all time and by far the best to never compete in the UFC. Back in 2008, UFC Heavyweight champion Randy Couture was all the rage in America and a Super fight between the two was rumored and even culminated in a staredown between the two and even Couture vacating his belt to go make the fight happen. The fight never was made based on egregious demands of Fedor's camp, but his interest would later resurface against another fighter we'll see later in the list.

7. Tito Ortiz

vs Dana White

You just had to be there in 2008 when Tito, Chuck and Dana transformed this sport from a niche following to a global phenomenon. Mostly due to the fantastic rivalry between Ortiz and Chuck but in no small part due to the President of the company and the Champion Ortiz's own rivalry. Famously wearing a "Dana is my b***h" t-shirt to the UFC 89 Weigh Ins, Ortiz was the first villain-esque superstar of the sport and a sort of "Steve Austin" to fans with how he stood up to the authority. This fight was teased by none other than Dana himself, calling out the champ on an internet vlog in 2008 and later claiming Tito faked an injury to get out of it.

6. Conor McGregor

vs Nate Diaz 3

So obviously we got to see McGregor-Diaz twice but after the media storm after their first fight and the epic encounter of their second, the fight's crescendo and trilogy was fantasized since their last meeting in 2016 all the way to this day. We'll never see it in the UFC now with Diaz's career at it's end and McGregor's also likely. Obviously, everything around McGregor at this time was dollar signs but the prospective trilogy for this rivalry would have made more money than any other fight on this list and it wouldn't even be close.

5. Georges St. Pierre

vs Khabib Nurmagomedov

When I said that most anticipated was the basis of this list, this fight may be the only one that's not completely within that criteria. In 2019, Khabib was undefeated and ruling the Lightweights and GSP hadn't fought in over a year. At the time, both of these men were among the Top-5 to ever compete in the sport and a move up from Khabib to Welterweight would have been epic. The negotiations broke down due to management from both sides but this fight was so close to being the only fight in history between two BONAFIDE Top-5 fighters in UFC history.

4. Jon Jones

vs Tom Aspinall

Photo by Youtube Screengrab/ Tom Aspinall MMA

The most recent "What If" on the list and one that theoretically could still happen was this prospective clash between Heavyweight and interim-Heavyweight champions in 2024. This fight was all about if Aspinall would finally be able to do what no one has ever done; beat Jon Jones. We may never know as it seemed Jon Jones was content to retire rather than defend his Heavyweight championship against the #1 contender. This "What If" is so layered that it deserves it's own article but for now, I'll leave you with this: Jon Jones was right to be scared.

3. Fedor Emelianenko

vs Brock Lesnar

The newer generation of fans won't really understand the next two fights but when I tell you the ENTIRE WORLD of MMA fans were salivating on this fight I'm not exaggerating. Fedor was the best Heavyweight in the world and Brock was the biggest draw the sport had ever seen. The fight between the two would have drawn millions from the United States and Russia as well as Japan and Europe alike. The fight didn't happen because Fedor literally asked for a stake in the UFC and was laughed out of the country but for about 4 months, this matchup was EVERYTHING.

2. Anderson Silva

vs Georges St. Pierre

Take the popularity of Fedor and Brock and the pure fight that would've been between GSP and Khabib and you have the 2011 potential of the Middleweight GOAT Anderson Silva vs the Welterweight GOAT Georges St. Pierre. In 2010 to 2011, these two were #1 and #2 in terms of the greatest UFC fighters ever and both in the midst of their record Win Streaks. With Georges clearing out his division, the thought was to have him move up and challenge for Anderson's title. This can't be overstated, this would've been King Kong vs Godzilla with 4-ounce gloves. This fight never got extremely close to getting booked because of a number of issues including GSP's demands for drug testing that would later result in the UFC working with USADA which would "pop" Silva only 4 years later.

1. Jon Jones

v Francis Ngannou

I still can't believe we didn't see this fight. The greatest fighter to ever live was moving up from his 12-year Light Heavyweight career to Heavyweight and was on a collision course with, (and this is no exaggeration) the scariest man in UFC history and the reigning Heavyweight champion. Factors like Jones' 3 year layoff to "become a Heavyweight the right way" and Ngannou's "exorbitant demands for this fight" (as told by Dana White) caused the UFC to not renew it's champion and the fight never went down. When you talk about fights that never happened across any combat sport, this is it. "Will Jones make it as a Heavyweight?", "Will Ngannou knock Jones out?" and "Can Jones become a 2-division Champ" were just some of the questions we pondered from 2020 to 2023.