Floyd Mayweather Hardest Fight

Floyd Mayweather went 50-0 in his legendary boxing career, but one fight stood out above the rest — and it wasn’t against Pacquiao, Canelo, or De La Hoya. In 2000, a little-known fighter named Emanuel Augustus gave Mayweather the toughest challenge of his life.

This video breaks down the wild, unpredictable clash between Mayweather and Augustus — a bout filled with nonstop action, awkward angles, and one of the rare moments Floyd was visibly hurt and bleeding. Known as “The Drunken Master,” Augustus brought a style no one could prepare for, and Mayweather had to dig deep to survive.

Watch as we relive the highlights, explore what made this fight so dangerous, and explain why even Mayweather himself called it the hardest fight of his entire career.

If you’re a fan of boxing history, underdog stories, or classic fight breakdowns, this is a must-watch. Subscribe to Boxing Now for more legendary fight analysis, rare highlights, and hidden gems from the fight game.

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⏰Time Stamps -
0:00 - Floyd Mayweather vs Emanuel Augustus
0:40 - Floyd Mayweather's Toughest Opponent
2:10 - Floyd Mayweather vs Emanuel Augustus Round 1
17:25 - Floyd Mayweather beats Emanuel Augustus

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