#4. Tyron Woodley vs. Stephen Thompson – UFC welterweight title (2017)

When the UFC signed a rematch between welterweight champ Tyron Woodley and top contender Stephen Thompson in early 2017, it made total sense. Not only had their first fight been declared a draw by the judges, but the fight itself was largely excellent, winning UFC 205’s Fight of the Night award.
Unfortunately, the fact that both men had made some adjustments going into the second bout meant that where the first was great, the second turned out to be remarkably dull, ruining UFC 209 entirely.
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Essentially, after being hurt badly by Woodley’s punches in the first fight, ‘Wonderboy’ simply appeared to respect him a little too much, refusing to engage and remaining on the outside where he picked at the champion with his strikes to little effect.
Woodley, meanwhile, was unable to really lay a glove on Thompson, outside of landing a single takedown in the third round and a crushing combination in the waning seconds of the fight that nearly put ‘Wonderboy’ out.
Outside of those moments, though, it’s not unfair to suggest that literally nothing happened in the entire bout. In the end, Thompson did so little overall that those two attacks from ‘The Chosen One’ were enough to persuade the judge that he deserved the nod, allowing him to retain his title.
Unfortunately for him, though, the performance did nothing for his popularity in general, and was basically enough to ruin his reputation with both the fans and the UFC’s brass for good.
#3. Kevin Randleman vs. Pedro Rizzo – UFC heavyweight title (2000)

When UFC fans discuss the worst heavyweight title fights in the history of the promotion, the fight that usually stands out is Tim Sylvia’s third clash with Andrei Arlovski from the summer of 2006. However, while that fight was undoubtedly dull, it can’t hold a candle to Kevin Randleman’s fight with Pedro Rizzo six years beforehand.
Bizarrely, the fight seemed cursed before it even began. Initially, the two men were supposed to headline UFC 24, only for Randleman to somehow knock himself out backstage while warming up by striking his head on a pipe.
The fight ended up taking place two shows later, but if the fans had expected a barnburner, they were painfully mistaken.
Rizzo’s reputation as a deadly counterstriker preceded him and so Randleman had evidently decided that his best course of action would be to avoid pressing the action at any cost. In turn, ‘The Rock’ seemed so afraid of Randleman’s takedowns – and so wedded to his counterpunching gameplan – that he did very little in return.
In the end, the fans were treated to a fight filled mostly with circling and staring, with the odd clinch thrown in for good measure. The bout went the distance, and while ‘The Monster’ retained his title via decision, the fact that the crowd decided to fill the octagon with trash in the final seconds told its own story.
Due to the show taking place in the depths of the UFC’s ‘Dark Ages’, this fight has largely been forgotten. To be honest, that’s probably for the best.