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3. Royce Gracie and Art Jimmerson

It’s amazing that Royce Gracie’s fight against a man wearing a boxing glove on one of his hands is only ranked #3 on this list.

Jimmerson was a talented boxer who won 33 fights in his pro career. In MMA however, he fought once and he lost once. That fight was at UFC 1 against Royce Gracie, where his infamous decision to wear a boxing glove on one of his hands will live forever in the lore of MMA’s pioneering days.

The boxing glove prevented Jimmerson from being able to defend on the ground against Gracie’s jiu-jitsu, but he probably wouldn’t have been able to defend much anyway.

YouTube video

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Gentleman Jeff
Ian is a MMA writer based out of Toronto, ON Canada. An avid mixed martial arts enthusiast and passionate fan since he was born, Ian has been writing about mixed martial arts for over 5 years.