Top 10 Upsets in Boxing History

Delve into the unpredictable world of boxing upsets with our curated list of the top 10 shocking moments in the sport’s history. From underdogs overcoming insurmountable odds to unexpected outcomes that left fans in disbelief, these upsets showcase the thrilling and unpredictable nature of boxing. Join us as we revisit some of the most memorable moments that shook the boxing world and forever changed the course of the sport.


Mike Tyson vs. Buster Douglas

The upset of all upsets, Buster Douglas shocked the world when he defeated the undefeated Mike Tyson in Tokyo, Japan, in 1990. Despite being a massive underdog, Douglas dominated the fight and knocked out Tyson in the 10th round, handing him his first professional loss and cementing his place in boxing history.


Muhammad Ali vs. Leon Spinks

In 1978, Muhammad Ali suffered a stunning defeat at the hands of Olympic gold medalist Leon Spinks. Despite being considered past his prime, Ali was expected to easily dispatch Spinks. However, Spinks’ relentless aggression and tenacity earned him a split decision victory, making him the only man to defeat Ali twice in his professional career.


James ‘Buster’ Douglas vs. Evander Holyfield

After his historic victory over Mike Tyson, Buster Douglas faced Evander Holyfield in a highly anticipated bout. Despite being the underdog once again, Douglas put on a valiant effort and went the distance with Holyfield, ultimately losing by decision. While he didn’t secure the win, Douglas proved that his victory over Tyson was no fluke.


Sonny Liston vs. Cassius Clay (Muhammad Ali)

In one of the most iconic upsets in boxing history, Cassius Clay, who later changed his name to Muhammad Ali, defeated Sonny Liston to claim the heavyweight title in 1964. Liston was heavily favored to win, but Ali’s speed, agility, and unorthodox style proved too much for the champion, leading to a stunning seventh-round TKO victory.


Hasim Rahman vs. Lennox Lewis

Hasim Rahman shocked the boxing world in 2001 when he knocked out Lennox Lewis to claim the WBC, IBF, IBO, and lineal heavyweight titles. Despite being a heavy underdog, Rahman landed a thunderous right hand in the fifth round that sent Lewis crashing to the canvas, handing him his first loss in eight years.


Jose Luis Castillo vs. Floyd Mayweather Jr.

In 2002, Jose Luis Castillo pushed Floyd Mayweather Jr. to the limit in their first encounter, earning a controversial split decision victory. Many observers felt Mayweather had done enough to win, but Castillo’s relentless pressure and effective aggression swayed the judges in his favor, handing Mayweather his first professional loss.


George Foreman vs. Muhammad Ali

In the famous ‘Rumble in the Jungle’ in 1974, Muhammad Ali stunned the world by defeating George Foreman to reclaim the heavyweight title. Foreman was considered unbeatable at the time, but Ali’s ‘rope-a-dope’ strategy, combined with his speed and resilience, proved to be the perfect formula for victory.


Andy Ruiz Jr. vs. Anthony Joshua

In 2019, Andy Ruiz Jr. pulled off one of the biggest upsets in recent memory when he defeated Anthony Joshua to claim the WBA, IBF, WBO, and IBO heavyweight titles. Ruiz, a late replacement for Joshua’s original opponent, shocked the boxing world by knocking down Joshua multiple times en route to a seventh-round TKO victory.


Joe Louis vs. Max Schmeling II

In their highly anticipated rematch in 1938, Joe Louis avenged his earlier loss to Max Schmeling with a devastating first-round knockout. Schmeling had defeated Louis two years prior and was seen as a symbol of Nazi Germany’s superiority. However, Louis’ emphatic victory not only redeemed himself but also served as a powerful statement against racism and oppression.


Evander Holyfield vs. Mike Tyson II

In their rematch in 1997, Evander Holyfield once again shocked the world by defeating Mike Tyson, this time via disqualification. Tyson, frustrated by Holyfield’s tactics, bit off a piece of Holyfield’s ear in the third round, resulting in a disqualification and handing Holyfield another unexpected victory over the former heavyweight champion.

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