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The Greatest Upsets in Boxing History

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It’s incredible how tables often turn in the boxing arena. You’ll see a boxer on an all-conquering spree felled to the floor by his challenger, written off by all in a matter of minutes.

Yes, that’s boxing, where stunning upsets have had bookies laugh all the way to the bank. There have been, and there will be many boxers capable enough to get the better of their more fancied opponents. We bring you what we consider are some of the biggest upsets boxing has ever seen; those that had the sports page headlines screaming the following morning. 

1. Mike Tyson’s Loss against Buster Douglas in 1990

The one to blame for this truly sensational upset is none other than Tyson himself. Mike Tyson was at the peak of his form and earned the nickname ‘The Baddest Man on the Planet.’ He was so confident that he didn’t even bother to train for the bout in Tokyo. 

Tyson’s overconfidence saw him partying during the build-up to the fight, and he arrived for it relatively unprepared. Douglas, written off at a 42/1, went groggy after a crushing uppercut from Tyson. However, he managed to gather himself and, after landing a barrage of stinging blows on Tyson, had him crash to the floor. After the match, Tyson had admitted that he did not see Douglas as a threat. He did not bother watching any of Douglas’ fights. Thus, his behavior led to him losing, which now is considered as the most unpredictable defeat in history.  

2. Sonny Liston Goes Down to Cassius Clay in 1964

Liston’s complete domination of the boxing ring saw hardly anyone giving Clay, who later became Muhammad Ali, any hope of pulling it off against Liston. However, Ali had a surprise up his sleeve. His ‘float like a butterfly, sting like a bee’ mantra came to the fore in this fight as he demolished the ‘Grizzly Bear’ Liston. Sonny ended up slumped on his stool after the eighth round drew to a close. 

3. Lennox Lewis Loses to Hasim Rahman in 2001

Lewis paid scant regard to Rahman and paid the price. He chose to stay back in America to redo his cameo appearance in Ocean’s 11, the Hollywood blockbuster, rather than arriving at South Africa early for acclimatization. The fallout: Lewis arrived completely unprepared to take on neither the man nor the environment and simply fell apart in the fifth round itself- a defeat hard to digest.

4. Max Baer Falls against James J. Braddock in 1935

This bout was the stuff of fairytales, and it spawned Hollywood’s one of the most popular sporting films ever. The ‘Cinderella Man’ Braddock was a rank outsider at 10/1 and stunned the world after tearing into the much-hyped Baer the moment the opening bell rang. There were theories of mob conspiracies in the air about the bout at Maddison Square Garden, but that doesn’t take away the fact that we were witness to one of the sports’ greatest moments when Max bit the dust. 

5. George Foreman’s Loss against Muhammad Ali in 1974

This fight makes it to our rankings as one of the most remembered bouts in the sport’s history. With Ali stepping into the twilight of his career and Foreman building up a reputation of an intimidating champion boxer, the ‘Rumble in the Jungle’ was expected to be a no-contest. However, Ali caused a sensation as he took blow after blow to ultimately exhaust Foreman and then flatten him in the eighth round. It was a stunning display of endurance. 

6. Mike Tyson falls to Evander Holyfield in 1996

At 1/25, Tyson was billed as the undisputed favorite heading into this bout against Holyfield. Holyfield had earned much adulation and admiration of boxing fans after deciding to make a comeback after quitting boxing due to a heart ailment in the early half of the ’90s. The admiration rocketed after Holyfield dished out a scintillating display of heavyweight boxing artistry and went on to achieve a TKO in the eleventh round. 


Boxing has given the world of sports some truly engrossing upsets. Those who looked indomitable have had to bite the dust falling to less fancied opponents. Some of these bouts have even spawned films that have inspired people a lot. The underdogs have at times come up with stunning displays of endurance and stamina to pull off major upsets. Stay tuned for more such fairytale fights.