The Worst

3. Mirko Cro Cop vs. Alistair Overeem
Dream Middleweight Grand Prix Final, September 23, 2008 – Saitama, Japan

Preceding the battle of possibly the two best heavyweight kickboxers in MMA was a heated war of words that started at Sherdog.com. Overeem challenged Filipovic, who had just returned to Japan after a hit-and-miss stint in the UFC, to a fight. Cro Cop’s battered body –- he would later undergo knee and elbow surgery -- prevented the fight from happening in July. In September, the quarreling couple was finally on a collision course though.

Overeem was hell-bent on using a potential victory over the ever-popular Cro Cop as his personal launching pad. In the fight, he brutally beat down the Croatian on the ground and cut him above the eyebrow. With Cro Cop visibly shaken, Alistair hunted for the kill on its feet. But he took one tip too many from Barnett’s second fight with the Croatian and kneed Cro Cop’s thighs and ribs repeatedly, until he drifted below the waistline.

Filipovic was unable to continue and the bout was ruled a no contest. The diagnosis afterward was a testicle that had been pushed into Cro Cop’s abdominal cavity. Though technically not a loss, Cro Cop was clearly getting the worst of the beating –- a sight rarely seen before this.

2. Mirko Cro Cop vs. Kevin Randleman
Pride Heavyweight Grand Prix First Round, April 25, 2004 – Saitama, Japan

Kevin Randleman is a lot of things. He’s a fantastic athlete, a highly decorated amateur wrestler, a charismatic entertainer, a former UFC heavyweight champion and a lucky devil who has escaped death more than once. One thing he has never been considered throughout his illustrious career is a dangerous striker, though. That perception changed, albeit just for one night, when the “Monster” feinted a takedown attempt and dropped Cro Cop with a huge left hand instead.

The loss put a significant spoke in Filipovic’s wheel. Cro Cop had just bounced back from his first career loss against Antonio Rodrigo Nogueira five months earlier and wanted to use the Pride Heavyweight Grand Prix as a vehicle to earn a title shot against defending champion Fedor Emelianenko. With this jaw-dropping first-round exit from the tournament, Cro Cop was relegated to fighting at the distinctly smaller Bushido events for much of 2004.

1. Mirko Cro Cop vs. Gabriel Gonzaga
UFC 70, April 21, 2007 – Manchester, England

There is nothing worse than getting beaten at your own game. Joe Calzaghe did it to Roy Jones Jr. last year when he thoroughly beat him in a fashion that RJJ had used to perfection in his prime. The same, only much worse, happened to Cro Cop in his sophomore appearance for the UFC. Even though his debut against Eddie Sanchez left a lot to be desired, the Croatian was rewarded with a title eliminator against Brazilian grappling ace Gabriel Gonzaga.

Gonzaga had a reputation as an elite Brazilian jiu-jitsu black belt who could punch a little. In other words, he was going into the fight with Filipovic as the clear underdog. Fans were all the more surprised when Gonzaga caught a kick and took Cro Cop down before unleashing some ground-and-pound. The “kick heard around the world” then left the Croatian twisted like a pretzel on the canvas and effectively ended Filipovic’s run as a top-10 ranked heavyweight.