Top 10 Boxing Upsets That Shocked the World
Boxing has always thrived on the unexpected. For all the talk of favourites, rankings, and form, nothing captures fans’ imaginations quite like a good old-fashioned upset. In a sport where one punch can change everything, underdogs sometimes rewrite history.
Here are my top 10 boxing upsets — the moments nobody saw coming but nobody could forget.
10. David Price vs Tony Thompson I (2013)
At the time, David Price was seen as Britain’s next great heavyweight hope — an Olympic bronze medallist with devastating power and an unbeaten record. Few expected veteran Tony Thompson to pose much threat. Price entered the bout as a heavy 7–1 favourite. But on the night, Thompson silenced the crowd with a second-round knockout that shattered Price’s momentum. A rematch was made — and ended the same way, only slower.
9. Amir Khan vs Breidis Prescott (2008)
Amir Khan had the nation behind him after winning Olympic silver in 2004 and storming through his early professional career. Big names like Ricky Hatton were already being mentioned. But all that came crashing down in 54 seconds when Colombian puncher Breidis Prescott exposed Khan’s still-questioned chin. The defeat reshaped Khan’s entire career and made Prescott a household name overnight.
8. Max Baer vs James Braddock (1935)
This upset was so dramatic it inspired a Hollywood film (Cinderella Man). James Braddock was a 10–1 underdog when he stepped in to face world champion Max Baer. But the journeyman defied every odd, outworked the champion, and took a unanimous decision to win the heavyweight crown — one of the sport’s greatest feel-good stories.
7. Nigel Benn vs Gerald McClellan (1995)
Despite being the defending champion, Benn was a 3–1 underdog heading into his seventh title defence against the fearsome Gerald McClellan — a man with 14 straight knockouts, many in the first round. What followed was one of the most brutal fights in modern boxing history. Benn was dropped in the first but roared back, eventually stopping McClellan in the tenth. The bout was voted the greatest fight of the 1990s but ended in tragedy: McClellan suffered a brain injury that left him permanently disabled.
6. Mike Tyson vs Evander Holyfield I (1996)
When Mike Tyson returned to reclaim the heavyweight throne, many assumed his reign would continue unchallenged. But Holyfield — seen by many as past his best — delivered a tactical masterclass, dropping Tyson in the sixth and stopping him in the 11th. The result stunned the world. The rematch, of course, ended in chaos when Tyson infamously bit Holyfield’s ear.
5. Roberto Duran vs Kirkland Laing (1982)
Roberto Duran was expected to make light work of British underdog Kirkland Laing — but Laing had other ideas. He boxed beautifully over 10 rounds and won a deserved split decision in a fight many believed he dominated. It was named Upset of the Year by The Ring, and remains one of the most overlooked shockers in modern boxing history.
4. Julio Cesar Chavez vs Frankie Randall I (1994)
Julio Cesar Chavez entered this bout undefeated in 90 fights — a seemingly invincible Mexican icon. Frankie Randall was seen as a solid but unspectacular contender. But with smart footwork and a solid jab, Randall exposed Chavez’s age and timing. Two point deductions for low blows didn’t help Chavez’s cause, and Randall walked away with a split decision and the WBC title. Chavez won the rematch, but the damage was done — the legend had finally been beaten.
3. Muhammad Ali vs Leon Spinks I (1978)
In just his eighth professional fight, Leon Spinks challenged Muhammad Ali for the heavyweight title. Most thought the Olympic gold medallist was being fed to the legend. Instead, Spinks out-hustled Ali over 15 rounds to win a split decision. The 15th round was later named Round of the Year. Ali would avenge the loss in their rematch — but the upset remains a career-defining moment for Spinks.
1. Mike Tyson vs Buster Douglas (1990)
The ultimate upset. Mike Tyson was the undisputed, undefeated heavyweight champion — feared and untouchable. Buster Douglas, a 42–1 underdog, was seen as cannon fodder. But in Tokyo, Douglas boxed with heart, purpose, and precision. Even after being dropped in the eighth, he rallied to stop Tyson in the 10th — shocking the world and ending one of boxing’s most dominant reigns.
Who would make your list? Share your thoughts on CMBoxing and join the conversation.
Some very good matches a blast from the past Braddock Ail a lot of dodgy chins ,not sure what you call the two boxer’s look really good the ones the start of yonr blog great stuff.