Biggest Boxing Upsets of All Time

In no other sport is the concept of the underdog, as well-defined as in boxing. It is hard to bet against a good boxer on a winning streak. Boxing is predictable when a good fighter is in the ring. For example, you had to have a suicide wish to go against ‘Iron’ Mike in the late 80s. 

But there have been memorable upsets that went against boxing fans’ expectations and also the bookies’ prices. Some of the betting odds for these predictions were crazy. This website showcases the best odds for all sports, including boxing. Here are some fights that made underdog bettors a happy lot.

Hasim Rahman vs. Lennox Lewis (4/22/2001)

This was a classic case of the lucky punch. There was nothing going for Rahman; Lennox was taller and a sharper boxer against Rahman’s clumsy style. Lennox had walked into the ring as the huge favorite with -2000 in odds. 

Lennox’ was clearly having the upper hand and enjoying it. He got a little too cocky. That lasted until the fifth round when Rahman landed a right howler that sent Lennox to the canvas, unable to beat the count.

Randy Turpin vs. Sugar Ray Robinson (7/10/1951)

Widely regarded as one of the best pound-for-pound fighters of the 20th century, Sugar ray had gone undefeated in 90 fights. In the other corner, Turpin had never fought past the eighth round and was a clear walkover. What the bookies and fans didn’t count on was that Sugar Ray was not in his best form because he was touring Europe. The younger Turpin had walked into the ring as a clear underdog with +2000 odds. Sugar Ray couldn’t perform in the last four rounds, and the Briton took the title. 

Andy Ruiz jr. Vs. Anthony Joshua (6/1/2019)

It was almost laughable to think that the short, pot bellied Ruiz had anything against one of boxing’s 2010s stars. The bookies confirmed his almost hopeless shot at the title favoring Joshua -2400. What they didn’t count on was the American’s grit, and Joshua’s misplaced cockiness. But four knockdowns in five rounds soon disabused him of that cockiness. The ref stopped Joshua’s drubbing in the fifth round. Ruiz couldn’t help but quip, ‘Everybody that bet on me is gonna make some serious money.’ 

Muhammad Ali vs. George Foreman (10/30/1974)

The ‘Rumble in the Jungle’ fight showed the world why Ali was the greatest. The boxing fraternity had counted him out as he was aging and was against a fearsome, hard-hitting opponent. Ali walked into the ring as a 4/1 underdog. Foreman’s brute strength had seen him go through 40 opponents undefeated.

Ali came to the ring with a plan. His ‘rope-a-dope’ tactic counted on tiring out the stronger Foreman. Ali took a beating that shocked over the 1 billion fans watching the match. He then rallied in round 8 when he had assessed that Foreman was tired. A massive right and a flurry of follow-ups put down Foreman on the canvas with a TKO.

Leon Spinks vs Muhammad Ali (9/15/ 1978)

Ali was coming into the ring with 15 undefeated fights, and a boxing career that had crowned him ‘The Greatest.’ Spinks had fought only 7 professional bouts and came into the ring as a +1000 underdog. But Spinks was younger and studied the champ’s rope-a-dope tactics very well. He went toe-to-toe with Ali for the fifteen rounds. In the end, the judges handed Spinks the title. 

James ‘Buster’ Douglas vs. Mike Tyson (2/11/1990)

Tyson was virtually unstoppable in the late 80s having gone undefeated in 37 pro fights. He was savage, strong, and knocked out his opponents by the third round. The boxing world had never seen a more brutal fighter. Having become the world’s youngest heavyweight champion at 19 years, Tyson was at the top of the food chain. 

Buster walked into the ring as a +4200 underdog. The bookies initially priced him +1200, but the fans threw so much Tyson money at them, it got to 42/1 against Buster as the fight started. But Buster proved he had the grit and determination to go toe-to-toe with the baddest man on the planet. The fight lasted 10 rounds; an unbelievable thing for Tyson’s fans. Tyson was unused to going that distance. In the 10th round, Buster rocked him with a big uppercut and followed up, knocking him to the canvas. 

Boxing rarely produces upsets when there is a favorite in the ring, but when it does, the show is spectacular. There have been thousands of upsets, but these fights are most memorable. 


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