20. Antonio Rodrigo Nogueiro (2011)
‘Big Nog’ was one of the first fighters to achieve success with both the PRIDE and UFC promotions. In 2008, Frank Mir defeated him in an upset to claim the interim heavyweight title. Almost three years later, ‘Minotauro’ had the opportunity to get revenge. Most people believed that the Brazilian was the better fighter and that Mir’s KO win was a freak result.

But Mir didn’t receive that memo. He put the series beyond doubt with an infamous win. Mir snapped Big Nog’s arm like a twig due to a vicious kimura. It hung by his side in the most horrifying, lopsided manner. The image permanently etched itself into the brains of watching fans. Luckily, the injury wasn’t life-threatening and there were no long-term health effects but it was such a nasty moment.