# The 14 Biggest Upsets in Boxing History

> Bookmakers got every one of these wrong. Some ended a reign, one ended an aura.

*By YPB Team · Published August 2, 2026 · https://youpick.best/ranking/the-14-biggest-upsets-in-boxing-history*

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## Current results (0 votes)

1. **Buster Douglas beats Mike Tyson**
   A 42-1 underdog knocked out the undefeated heavyweight champion in Tokyo in February 1990.
2. **Cassius Clay beats Sonny Liston**
   The 22-year-old challenger took the heavyweight title from Liston in Miami Beach in February 1964 as an 8-1 outsider.
3. **Hasim Rahman beats Lennox Lewis**
   Rahman knocked out the undisputed champion in the fifth round in South Africa in 2001.
4. **Muhammad Ali beats George Foreman**
   Ali, a 4-1 underdog at 32, stopped the unbeaten Foreman in Kinshasa in 1974.
5. **Lloyd Honeyghan beats Don Curry**
   The British welterweight travelled to Atlantic City in 1986 and stopped the pound-for-pound number one.
6. **Randolph Turpin beats Sugar Ray Robinson**
   Turpin outpointed Robinson over 15 rounds in London in 1951 to take the middleweight title.
7. **Evander Holyfield beats Mike Tyson**
   Holyfield, a 25-1 underdog, stopped Tyson in the eleventh round in Las Vegas in 1996.
8. **Andy Ruiz Jr. beats Anthony Joshua**
   A late replacement dropped Joshua four times at Madison Square Garden in 2019.
9. **Leon Spinks beats Muhammad Ali**
   Spinks, in only his eighth professional fight, took the title from Ali on a split decision in 1978.
10. **James J. Braddock beats Max Baer**
   The Cinderella Man came off the relief rolls to outpoint Baer for the heavyweight title in 1935.
11. **Tyson Fury beats Wladimir Klitschko**
   Fury outboxed the long-reigning champion in Dusseldorf in 2015 to end a nine-year title run.
12. **Bernard Hopkins beats Felix Trinidad**
   Hopkins, the underdog, stopped the unbeaten Trinidad at Madison Square Garden in 2001.
13. **Jorge Castro beats John David Jackson**
   Castro was being outboxed and badly hurt before knocking Jackson out in the ninth round in 1994.
14. **Corrie Sanders beats Wladimir Klitschko**
   The South African southpaw dropped Klitschko four times and won inside two rounds in 2003.

Tags: sports, boxing, all-time, fighters