
4. (tied) Michael Bisping (+525) Upsets Luke Rockhold UFC 199
Considering that Rockhold had already defeated Bisping, and the Count was taking the fight on short notice, it’s surprising he wasn’t a bigger underdog.
Many, including Rockhold, claim that he failed to take Bisping seriously. In fact, very few did, which is why Bisping came into this bout as a +525 underdog.
This bout was supposed to be the rematch between Chris Weidman and Luke Rockhold from UFC 194, but Weidman was forced to pull out. Bisping KO’d him at 3:36 of the 1st round, winning the middleweight championship and making a few gamblers happy in the process.