30. Daniel Cormier vs. Brock Lesnar
It’s safe to say things didn’t work out for Daniel Cormier at UFC 241, but it goes beyond losing the heavyweight title to Stipe Miocic. When Cormier knocked out Miocic for the strap at UFC 226, he called out former heavyweight champion Brock Lesnar, who was sitting cageside. The ball started rolling towards a summer 2019 matchup between Cormier and Lesnar, but Lesnar ultimately stayed retired from MMA and re-joined the WWE. The reason for this matter reportedly was because Lesnar’s potential UFC earnings were less than he hoped thanks to the new ESPN+ pay-per-view deal. There’s not a complete possibility this would’ve been as competitive on some of the other fights on this list — Lesnar only had a one-fight comeback at UFC 200 since his retirement at the end of 2011 — but the build-up and uniqueness of this fight could’ve made it one to watch. Maybe we’ll get this in a WWE ring one day.
29. Donald Cerrone vs. Joe Lauzon
Want to talk about a fight of two popular UFC figures unwilling to hold back and always looking for a war? It’s kind of disappointing that despite all their time in the UFC’s lightweight division, we never got to see Donald “Cowboy” Cerrone and Joe Lauzon. Cerrone is perhaps one of the greatest UFC fighters to have never won gold, holding the records for most wins, finishes and post-fight bonuses in UFC history. Lauzon never had the greatest win-loss record this decade — when Cerrone began his rise up — but his post-fight bonus track record is another story. He has seven Fight of the Night honors, six Submission of the Night honors (a solidified UFC record), a Knockout of the Night, a Performance of the Night and the 2012 Fight of the Year (vs. Jamie Varner). He and Nate Diaz are currently tied for second-most post-fight bonuses (behind Cerrone). If a prime Cerrone and prime Lauzon ever did battle, no question it’d probably earn both men more bonuses.
28. Justin Gaethje vs. Joe Lauzon
This one is even more of a “past vs. present” bout of two warriors — simply because Justin Gaethje never got to the UFC until Lauzon was way on the twilight of his career. We’ve racked up Lauzon’s post-fight bonuses already, and while Gaethje doesn’t have much UFC experience, he certainly has impressed already since his 2017 debut. The previously-unbeaten Gaethje already has four Fight of the Night bonuses and two performance bonuses — becoming the first UFC fighter to win post-fight bonuses in all of his first five fights. Several media have even given him Fight of the Year and Round of the Year honors in his fights with the likes of Michael Johnson, Eddie Alvarez and Dustin Poirier. A fight between these two — with Lauzon in his prime — might not go the distance, but it’d be a war for no matter how long it lasted.
27. Jon Jones vs. Anthony Johnson
The fact Jon “Bones” Jones vs. Anthony “Rumble” Johnson never ended up taking place is quite the tragedy, especially for fans of the light heavyweight division. These two were scheduled to face off at for the 205-pound title at UFC 187, but Jones would be stripped of the title and suspended indefinitely thanks to his 2015 hit-and-run incident. Johnson ended up losing to Daniel Cormier for the vacant title and lost to DC again at UFC 210 before leaving behind MMA. One has to wonder if these two did end up meeting in May 2015 — or if Johnson beat Cormier and faced Jones in 2017 — if Johnson ends up being the one to end Jones’ dominance. This fight technically could still happen if Johnson’s 2020 comeback holds true and he drops back down to 205 or Jones moves up to heavyweight — but it won’t have the same magic as if they had the UFC 187 fight.
26. BJ Penn vs. Randy Couture
BJ Penn and Randy Couture were the first to pull off a significant feat — win UFC titles in two different weight classes. In fact, if it weren’t for these two, perhaps Conor McGregor, Daniel Cormier, Amanda Nunes and Henry Cejudo never go for champ-champ status. Penn won the welterweight title in 2004 and the lightweight championship in 2008, while Couture won the UFC heavyweight title three times and the light heavyweight title twice. Both are UFC Hall of Fame members, both have fought past their inductions and the age of 40, and both have at one point left the promotion in a contract dispute. So, wouldn’t a fight between these two pioneers be fun?