50. Jon Jones vs. Dan Henderson
Jon Jones and Dan Henderson were scheduled to face off in a light heavyweight title bout to headline UFC 151 in 2012. Henderson, however, was forced out nine days prior to the event with an injury. With Jones rejecting a late-notice fight with Chael Sonnen, UFC 151 became the first event in UFC history to be canceled. Jones and Henderson would face off in a December 2016 Submission Underground event, which Jones won, but one has to wonder how the fight would’ve played out if they were in a cage and allowed to strike.
49. Michael Bisping vs. Yoel Romero
When Yoel Romero and Michael Bisping exchanged pleasantries with one another following Romero’s knockout of Chris Weidman at UFC 205, it looked to be the start of a fun ride towards a middleweight title bout between the two. But Bisping ended up getting hurt and pushed for a fight with Georges St-Pierre, who hadn’t been seen in four years. Romero, meanwhile, took on Robert Whittaker in an interim middleweight title fight at UFC 213. And unfortunately for fans of this matchup, both men lost their respective matches and Bisping would officially retire in May 2018. One has to wonder who would’ve come out on top had these two faced off. And had this fight occurred with GSP not inserting himself into the picture, would Romero have captured UFC gold?
48. Chan Sung Jung vs. Doo-Ho Choi
Chan Sung Jung and Doo-Ho Choi are both Korean MMA fighters with amazing nicknames — “The Korean Zombie” and “The Korean Superboy.” And both are featherweights who have been in wars and scored performance bonuses more than once. Jung has won a post-fight bonus in all but one of his seven UFC bouts, and he’s the lone featherweight in UFC/WEC history with two KO/TKO wins in under a minute. Choi, meanwhile, is 3-2 in the Octagon, which includes three first-round finishes (one 18-second win and two performance bonuses). His two losses saw him earn Fight of the Night bonuses — with the UFC 206 bout with Cub Swanson earning Fight of the Year honors as well. Choi is currently inactive, serving a mandatory two-year military service — the same Jung once had to serve. But as long as Choi comes back, and he’s still the “Superboy” he was when he left, could we possibly see a UFC event in Korea headlined by these two? Sounds like a fun scrap.
47. Andrei Arlovski vs. Alexei Oleinik
Andrei Arlovski is perhaps one of the most recognizable names the UFC’s heavyweight division has ever had. Arlovski won the interim UFC heavyweight title at UFC 51 before getting promoted to undisputed champion and defending it once before dropping it in his latter two fights with Tim Sylvia. Arlovski left the UFC a couple of years later, and things looked bleak after four straight losses between Affliction and Strikeforce, but Arlovski got back to winning ways, and he made an amazing UFC comeback in 2014-15. The Sambo background of “The Pitbull” might present an interesting matchup with Alexei Oleinik, a fellow experienced MMA fighter with the style. Oleinik may not have the gold Arlovski has held, but Oleinik has earned popularity for finishing a UFC bout with an Ezekiel choke not once, but twice.
46. Alistair Overeem vs. Mirko Cro Cop 2
Alistair Overeem vs. Mirko “Cro Cop” Filipovic has happened before — but the end result left a lot to be desired. The two clashed at DREAM 6 in September 2008, but the bout was called a No Contest just over six minutes into the first round thanks to a couple of knees to the groin from Overeem to Filipovic. A rematch never took place, as Overeem went on to the UFC and Filipovic’s career went in another direction before its permanent end this year. Both men are kickboxing greats with some deadly striking, and it’s unfortunate we never got a clear-cut determination of who the better fighter is in a rematch.