The 10 Worst Fights in UFC History

The title says it all. These are what I think are the worst fights in UFC history.

I have only been a fan of the sport for since 2006 and only an avid fan for two years, so I haven't seen every fight out there. If you UFC aficionados can think of anything I didn't include, feel free to point it out.

I tried to only include main events, or at least fights with a lot of hype around them. I'm sure there have been a lot of terrible fights on the undercards, but those aren't the fights the fans pay to see, so it's not as big a deal when they suck.

Heath Herring vs Jake O'Brien (UFC Fight Night 8)

Heath Herring was supposed to be a big prospect for the UFC's heavyweight division. It had been talked about for some time that the division lacked substance, and so the former PRIDE fighter was brought in to add some depth to the division.

However, things didn't go exactly according to plan.

Herring displayed terrible takedown defense as well as ground defense throughout the whole fight.

O'Brien took him down at will and passed his guard easily, spending most of the fight in dominant positions.

Unfortunately, O'Brien was content with the fact that he was winning the fight based on position and did very little damage with his superior positions and took very few (if any) risks.

Herring's inability to stop O'Brien's takedowns and O'Brien's reluctance to try and finish the fight made for a real snoozer.

Randy Couture vs James Toney (UFC 118)

There was a lot of hype surrounding this fight, but anyone who knew anything about MMA knew what was going to happen.

Couture got a takedown 15 or so seconds into the fight and dominated Toney on the ground, eventually sinking in an arm triangle choke to end the fight.

Why anyone thought Toney had a chance in MMA when he had no prior grappling experience is beyond me.

This was probably the least competitive fight in UFC history.

Tito Ortiz vs Ken Shamrock 3 (UFC Fight Night 6.5)

This fight was simply one of the most unnecessary in UFC history.

Before this fight, Tito had already beat Ken twice. One time was a decisive corner stoppage, and the other was a slightly controversial early stoppage by the referee.

However, in the fight that was stopped early it was clear that Tito was winning and if the fight had gone much longer, the result would likely have been the same, but without the controversy.

Not surprisingly, the third fight looked much the same as the first two. Tito beat Shamrock easily, winning by first round TKO.

The fight was far from competitive, and everyone knew what was going to happen. Also, the build up to the fight was kind of annoying to watch, because both men are bad at trash talking.

I believe this is the only trilogy in UFC history where one fighter lost all three fights.

Ken Shamrock vs Dan Severn (UFC 9)

This fight has the same problem as a lot of fights on the list: inactivity.

Much of the fight was these two circling each other, over and over. Very few punches landed standing.

The ground portion of the fight was equally un-entertaining.

Just a really boring fight.

Frank Mir vs Mirko Cro Cop (UFC 119)

Considering the amount of potential this fight had to be great, it's sad just how terrible it was.

Crop Cop is one of the most devastating strikers in the history of MMA and Frank Mir is one of the most talented heavyweights ever.

Stylistically, it was an awesome match-up.

Unfortunately, both men are likely near the end of their careers (Mirko more so than Mir) and both fought like they were aware of that.

Both men seemed afraid to lose and hardly engaged each other throughout the whole fight.

The fact that this fight ended with a vicious third-round KO, and I still hate it, speaks volumes to how bad it is.

Randy Couture vs Brandon Vera (UFC 105)

Randy Couture is one of the greatest strategists in the history of the UFC, if not the greatest.

While the game plans he develops are always intelligent, they are not always entertaining.

Couture knew that he was outmatched standing and that he'd have a hard time getting Vera down, Vera having a strong background in Greco-Roman Wrestling.

With that knowledge, Couture decided his bet for winning this fight was to keep Vera pressed up against the cage and work his dirty boxing.

He won the fight, but very few fans enjoyed seeing Couture try to pin Vera against the cage for 15 minutes.

Tim Sylvia vs Andrei Arlovski 3 (UFC 61)

In this fight, we saw two fighters refusing to engage for fear of being embarrassed by the other.

In their first fight, Arlovski rocked Sylvia early and then caught him with a heel hook.

In the second fight, it looked like Arlovski was going beat Sylvia again, but after being rocked, Tim mustered a comeback, knocking Arlovski out in devastating fashion.

In the third fight, both men knew the other had the tools to beat them and so they were remarkably hesitant.

The really horrible part is it was a five-round fight.

Chris Leben vs Michael Bisping (UFC 89)

Much like the fight between Couture and Toney, this fight was not at all competitive. The difference is it went all three rounds.

During those three rounds, we saw Michael Bisping moving backwards and hitting Leben with little punches (which eventually added up to some decent damage, as you can see in the photo). Leben was confused and completely stifled by Bisping's game plan.

Regrettably, it was just not fun to watch Chris Leben walking forward and accomplishing nothing for three rounds.

Anderson Silva vs Demian Maia (UFC 112)

In this fight, we saw Anderson establish in the first few minutes that he could beat Damien Maia whenever he wanted to.

Then he danced around the cage for four and a half more rounds.

Enough said.

Anderson Silva vs Thales Leites (UFC 97)

The photo here pretty much sums up the fight.

Thales was absolutely terrified of engaging with Anderson on the feet. Throughout this five-round ordeal Leites avoided contact with Anderson as much as possible and took every opportunity to fall on his back and try and lure Anderson into his guard.

This list has no specific ranking system, but this was probably the least entertaining fight in UFC history and perhaps in MMA history.

Honorable Mentions

Tim Sylvia vs Brandon Vera

Quinton Jackson vs Rashad Evans

Quinton Jackson vs Lyoto Machida

Royce Gracie vs Harold Howard

Ken Shamrock vs Royce Gracie 2