5. Randy Couture vs. Wanderlei Silva
In 2003, Randy Couture, approaching the age of 40, made the decision to drop down to light heavyweight. Despite the thoughts of plenty, it paid off, as Couture bested Chuck Liddell for the interim light heavyweight title before defeating Tito Ortiz to become the undisputed champion. A freak injury caused him to drop the title to Vitor Belfort, but he regained it at UFC 49 in August 2004. After the win, Couture called someone out, but it wasn’t a superstar of the UFC (not yet, at least) — it was PRIDE middleweight champion Wanderlei Silva. Around the time Couture dropped to 205 pounds, Silva was dominating in the Japanese MMA promotion. He was unbeaten in PRIDE before a loss to Mark Hunt on New Year’s Eve 2004, and he never dropped the middleweight belt until a loss to Dan Henderson in 2007. In the Octagon at UFC 49, Couture teased a title unification bout, but it ultimately never happened. And unfortunately, Couture and Silva never faced off at all.
4. Ronda Rousey vs. Cris Cyborg
Ronda Rousey and Cristiane Justino (aka Cris Cyborg) are two of women’s MMA’s most dominant forces in history. Plenty dreamed of these two facing one another, but it looks like with high bad blood and Rousey now in WWE, such a fight will only live in fans’ and promoters’ dreams. While Rousey had experience competing at featherweight, she was known as, and most comfortable, at bantamweight — a division which Justino has stated she’d struggle to take (heck, she struggled to make 140 pounds early in her UFC run). And following Justino’s failed drug test at the start of 2012, Rousey expressed she had no desire to compete against “Cyborg” ever.
3. Khabib Nurmagomedov vs. Tony Ferguson
It feels like a crime that this fight — despite all the real chance it could be made once again if Nurmagomedov successfully defeats Dustin Poirier at UFC 242 this coming weekend — has never taken place. The bout was scheduled for 2015, but Nurmagomedov got injured. The fight was booked in 2016, but Ferguson got injured. The fight was booked for UFC 209 in 2017, but Nurmagomedov was hospitalized after a bad weight cut. Finally, the fight was booked for UFC 223 in 2018, and Ferguson ends up pulling out after a freak accident injures him. Nurmagomedov has been one of the most dominant competitors the lightweight division has ever seen, and Ferguson has scored win after win. These two are the best lightweights the UFC has to offer, and even if Conor McGregor tries to get back into the title picture, Nurmagomedov vs. Ferguson must happen. It. Has. To. Happen.
2. Khabib Nurmagomedov vs. Georges St-Pierre
Khabib Nurmagomedov has dominated all his opponents, thanks to superior takedown and wrestling, as well as the pressure he brings. No one has seemed to figure out how to neutralize his abilities and tire “The Eagle” down. But there was once a time where Georges St-Pierre was able to make his opponents’ gameplans ineffective, and he dominated 170 pounds for years. Rumors of a showdown between Nurmagomedov and GSP swirled between 2018 and 2019, but ultimately negotiations fell through and GSP retired for good earlier this year. Judging how GSP did against Michael Bisping after four years away from the Octagon, he may have provided a true test for Nurmagomedov, whether it’d be at 155 or 170. And if a prime Nurmagomedov faced a prime GSP, who knows which way the fight would have fallen in favor of.
1. Georges St-Pierre vs. Anderson Silva
There was once a time where Georges St-Pierre and Anderson Silva looked unstoppable. These men held dominant reigns over the promotion’s welterweight and middleweight divisions, respectively. At one time, fans hoped to see GSP move up in weight and see if he could give Silva a run for his money and hold two titles (this was the pre-McGregor era, keep in mind). But such a matchup never came to fruition, and in 2013, Silva dropped his title to Chris Weidman and GSP left the sport for four years. There were teases since GSP’s one-fight comeback for UFC 217 that these two could meet, but the magic — and most likely the fight quality — would not be the same as if they had a champion vs. champion meeting in the late 2000s or early 2010s.