What’s the Greatest Win in Boxing History?

[TIC]

roberto duran over sugar ray leonard in montreal

[The Six Four]

Great picks,

Master, Joe Louis’ first-round destruction of Max Schmeling in their rematch wasn’t just a win—it was a statement that made him a national hero. Given the political backdrop, the fight carried immense significance, and Louis delivered in devastating fashion. That performance cemented his legacy as a true icon.

Mark TKO, Buster Douglas’ knockout of Mike Tyson in Tokyo is the definition of a shocker. At the time, it felt impossible, Tyson carried the "Baddest Man on the Planet" aura, seen as unbeatable. But behind the scenes, he was unraveling, and driven by personal tragedy, Douglas delivered an incredible performance, putting it all together when it mattered most. Definitely one of those "where were you when it happened" moments.

TIC, absolutely, Sugar Ray was the Golden Boy, but Duran refused to play into that. He broke Leonard mentally before they even stepped in the ring, forcing him into a toe-to-toe war that suited Duran perfectly. That mental warfare leading up to the fight was next level, and Leonard played right into it. A great fight and an even greater win for Duran.

[Master]

Joe Frazier beating Ali in the biggest boxing event of all time where 2 active undefeated heavyweight champions faced one another. Two different personalities and styles but both winners. Everyone in the world wanted to watch this event and even Frank Sinatra could only get a seat if he took photographs.

Labelled the Fight of the Century lived up to the hype. Joe was not going to be denied that night and put so much pressure on Ali that led to that brutal left hook landing in the last round to make certain of his victory. If Frazier had to win one of their tribology then that first battle would be it.

[X]

​Jack Johnson defeating James J Jeffries …….

[The Six Four]

More great suggestions,

Master, an excellent choice—Frazier vs. Ali in the Fight of the Century absolutely lived up to the hype. Two undefeated champions battling for supremacy in a truly historic showdown.

X, Jack Johnson’s win over Jeffries was another monumental moment. That fight, also billed as the Fight of the Century, carried immense historical and racial significance, making it one of the most anticipated bouts ever.

If I may play devil’s advocate on some of the fights mentioned—Schmeling was a former champion and considered past his prime when he faced Louis in the rematch, and Jeffries was coming off a six-year retirement, despite being the betting favorite. Unlike Foreman against Ali, Tyson against Douglas, or Leonard against Duran, they weren’t seen as being at their peak.

Was Ali past his prime going into the first Frazier fight? And should we consider Tyson at his peak against Douglas as well? What do you think?

[Alpha]

Duran over Barkley was a masterclass in skill and toughness, Foreman’s KO of Moorer was the ultimate reminder of his power, and Turpin’s victory over Robinson was a historic triumph that shook the sport. Three legendary wins that showcased heart, resilience, and greatness.

[Master]

Good questions and people can always criticise any fight if they are inclined and looked hard enough.

All I can say is that Max did not lose to anyone else in between beating and losing to Joe Louis so think he was not that far from his peak at 33 years of age. I never understood why Schmeling did not get the world title shot after he beat undefeated Joe which was only 2 years earlier.

I think X meant Jack Johnson beating the first great white hope and causing race riots across the US was a great win.

Ali was not past his prime going into the first Frazier fight as he had great wins after that fight. Although it could be argued that he was not seasoned/active enough to beat Joe the first time after the ban from the sport.

Mike Tyson career peaked before Douglas when he was with Kevin Rooney. He went downhill after that losing his discipline, desire and spirit. Problems with management, marriage and promoters took their toll on his career and he looked poor against Buster.