- One of the biggest upsets in boxing history was the win of James Douglas over Mike Tyson in 1990.
- Max Schmeling, Hasim Rahman, and Andy Ruiz are also boxers included in this list of biggest upset wins.
- All upsets on the list are from the heavyweight division.
Part of the excitement of boxing is the Cinderella stories of massive upsets by underdogs. Throughout the history of the sport, we’ve witnessed several upset victories that forever changed the course of boxing.
Today, I listed the four biggest upsets in boxing history, in which four boxers defied the boxing odds and pulled off the improbable by taking down their heavy favourite opponents and walking away with the victory.
Biggest Upsets in Boxing History
| Fight | Date | Winner |
|---|---|---|
| James Douglas vs. Mike Tyson | Feb. 11, 1990 | Douglas via 10th-round knockout |
| Max Schmeling vs. Joe Louis | June 19, 1926 | Schmeling via 12th-round knockout |
| Hasim Rahman vs. Lennox Lewis | April 22, 2001 | Rahman via fifth-round knockout |
| Andy Ruiz vs. Anthony Josuha | June 1, 2019 | Ruiz via seventh-round TKO |
James Douglas vs. Mike Tyson
During the 80s and 90s, Mike Tyson was not only the IBF, WBA, and WBC heavyweight champion but was also the face of boxing because he left a devastating trail of destruction in the division to become the undisputed heavyweight king with multiple knockout wins.
Today in 1990, Buster Douglas defeats Mike Tyson. Betting odds were 42-1.
— TodayInSports (@TodayInSportsCo) February 11, 2023
In February 1990, Tyson was matched with James Douglas, who was a 42-1 underdog. He was expected to run through him much like he had with his previous opponents. However, it was the complete opposite, as Douglas engineered a massive upset by knocking Tyson out in the seventh round of their match to become the new king of the weight class.
Max Schmeling vs. Joe Louis
Joe Louis was a force to be reckoned with during his prime years in the 1930s when he was an undefeated boxer in the heavyweight division. He was touted as the sport’s next superstar because of his incredible knockout power, which obliterated his opponents one by one.
However, Max Schmeling momentarily halted his ascent by scoring a shocking 12th-round knockout finish in their June 1936 encounter. Schmeling utilized a counter-punching strategy that frustrated Louis and eventually led him to the big win. Schmeling was a 10-1 underdog before their match but was able to defy the odds and get the victory.
Hasim Rahman vs. Lennox Lewis
In 2001, Lennox Lewis was the reigning undisputed heavyweight champion of the world and was riding a 13-fight win streak when he fought Hasim Rahman for his fifth world title defence of the IBF, WBO, and WBC world titles.
Due to his recent form and dominant performances, Lewis was a considerable -2000 favourite in the match against Rahman. But the challenger had other plans that night and mustered a big victory against Lewis by stopping him in the fifth round of their world title showdown via knockout.
Andy Ruiz vs. Anthony Josuha
Anthony Joshua was supposed to be the next big thing in boxing after he unified all the major world titles in 2018. But in December 2019, Joshua was pitted against Andy Ruiz for his second defence of his undisputed crown.
Joshua was the heavy -2400 favourite in the match not only because of his perfect professional record, but also due to the fact that he looked fitter than Ruiz, who didn’t have a muscular build like him.
Despite these circumstances, Ruiz surprised the boxing world by beating Joshua and scoring a seventh-round TKO loss to win all the championships. He also etched his name in the history books with a momentous upset.