20. Stipe Miocic vs. Cain Velasquez
Some newer fight fans may find it hard to believe that in the time between 2014 — when Stipe Miocic began his rise — and the end of 2016 — when Velasquez began a hiatus from MMA competition due to injuries, these two men never squared off with one another. Both men were NCAA wrestlers, but both also developed great striking power and ground work. If the Miocic dominating the heavyweight division were around when the likes of Velasquez, Junior dos Santos and Fabricio Werdum were all jockeying for the title, one could only imagine what this fight would have brought — and if Miocic could have stopped Velasquez like he did Werdum and JDS.
19. Stipe Miocic vs. Randy Couture
After Stipe Miocic won back the UFC heavyweight title at UFC 241, plenty considered him as solidifying his status as the greatest heavyweight in UFC history. He is one of just four fighters to have held the UFC heavyweight crown twice and is the only one to have successfully made three consecutive defenses of the strap. One has to wonder how his wrestling and boxing would fare against a prime Randy Couture. Couture, also a phenomenal wrestler, was one of the greatest fighters, let alone heavyweights, in promotion history. Couture was a three-time champion with three total successful defenses, the only man to have won a UFC title after turning 40 and the only one to regain titles he lost three times (one of those being at light heavyweight).
18. Alistair Overeem vs. Cain Velasquez
Alistair Overeem and Cain Velasquez were once both the heavyweight champions of rival promotions — Strikeforce and the UFC, respectively — in the early 2010s. The two could have faced off at some point after Overeem jumped to the UFC at the end of 2011, but Overeem ended up getting suspended after his debut and lost his next two fights. Just as Overeem started to get his feet under him in the Octagon, Velasquez dealt with injuries, dropped the UFC heavyweight title and has rarely fought since. Would Overeem’s kickboxing, or Velasquez’s wrestling come out on top here?
17. Jon Jones vs. Cain Velasquez
This fight appeared in my fights that could happen in 2019 piece, but with Cain Velasquez’s loss to Francis Ngannou and heart more in pro wrestling right now — along with Jones’ perceived lack of desire to move up to heavyweight yet and Daniel Cormier (Velasquez’s friend and teammate) losing the heavyweight title recently — this one looks more and more unlikely to happen. Even then, it’d probably be more exciting back in 2012-15, when each man dominated their respective divisions and held gold. Still, if this fight happened today, eyes would still need to be on it, as Cormier would certainly be in Velasquez’s corner, which could spark fireworks. And a Jones win over Velasquez could ultimately help build a desired Jones-Cormier trilogy bout — so long as Cormier doesn’t retire.
16. Joanna Jedrzejczyk vs. Ronda Rousey
For two years, Joanna Jedrzejczyk dominated the women’s strawweight scene in the UFC. And while her reign went into Amanda Nunes’ time as UFC women’s bantamweight champion, Nunes was still gaining momentum towards being the baddest female fighter on the planet. But once upon a time, that title belonged to Ronda Rousey, and both Rousey and Jedrzejczyk spent most of 2015 as the two best, most dominant female fighters in MMA. So imagine if the Jedrzejczyk and Rousey from the first half of 2015 fought one another in a champion vs. champion clash. Who’d come out on top? How good of a test would Jedrzejczyk give Rousey? Or would Rousey run through her as she did to bantamweight competition before running into Holly Holm?