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The Three Biggest Upsets in Heavyweight History

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Watford-born boxer Anthony Joshua is currently preparing to take on Andy Ruiz Jr. for a second time, this time to regain his titles.

The two touched gloves in June when the American was very much the underdog. In one of boxing history’s biggest shocks, the chubby Ruiz won by technical knockout, giving AJ the first professional loss of his career.

Where does that upset rank in heavyweight history? Read on, as we look back at the biggest fights where the winner upset the odds.

  1. Mike Tyson v Buster Douglas (February 1990)

The two met in Tokyo with the bout billed as “Tyson is back.”

‘Iron Mike’ was the undisputed heavyweight champion of the world, with an undefeated record of 37-0. Despite issues outside of the ring, he was still a force within the four ropes. James ‘Buster’ Douglas was ranked seventh by The Ring magazine and despite winning his previous six bouts, he had a mixed record of success: 29-4-1. Tyson was the overwhelming favourite (1/42) ahead of the fight.

It was an even contest until Tyson dropped his opponent in the eighth round. Douglas managed to beat the count and in the tenth round, landed a four-punch combination. Tyson hit the canvas for the first time in his career, although at the time of the knockout, he was winning on the majority of the judges’ cards.

Buster may have won the WBA, WBC, IBF, and lineal heavyweight titles, but he lost them all in his following match against Evander Holyfield.

  1. Mike Tyson v Evander Holyfield (November 1996)

When Tyson met Holyfield, it was a fight that had been a long time coming, so much so that it was billed as “Finally”. The bout saw WBA’s heavyweight champion ‘Iron Mike’ (45-1) take on the boxer ranked second, with a record of 32-3. Tyson’s previous four matches had seen him record a 100%-win rate and he was the 1/25 favourite. Holyfield had only won two of his last four bouts. 

But Holyfield silenced the critics and came out strong, retaliating to the punches Tyson threw. As the rounds progressed, ‘The Real Deal’ outmuscled and outpunched his rival, scoring a late stoppage. In the post-match conference, Tyson said to Holyfield: “Thank you very much. I have the greatest respect for you.”

We all know what happened in the rematch… But for those that are too young to remember, here’s a clip from “Bite Fight”.

  1. Anthony Joshua v Andy Ruiz Jr. (June 2019)

Ruiz made history as recently as June when he overcame the undefeated and unified heavyweight world champion Joshua. The Brit had been set to face fellow undefeated heavyweight Jarrell Miller but Miller failed several drug tests, and Ruiz was his replacement.

Joshua’s record of 22-0 boasted 21 wins by knockout, while ‘The Destroyer’, who was largely unknown, had an admirable record of 32-1 (21 KOs). He had previously battled for the vacant WBO belt, losing to Australian Joseph Parker by majority decision.

In the lead-up to the contest, the talk was firmly focused on the American’s physique with many calling it an easy win for AJ and most bookmakers had him at odds of 1/24. But Ruiz stunned the crowd both at Madison Square Garden in New York and those millions watching on at home. Joshua hit the canvas several times from the third round onwards and was never able to recover. In the seventh round, he received a knockout blow. With arms resting on the ropes and a bleary-eyed expression, the referee had no option but to call off the contest. 

The Destroyer made history in becoming the first boxer of Mexican heritage to win a heavyweight title in what was the shock of the century so far.

Although you’ll get favourable Anthony Joshua odds, as we have seen, occasionally the underdog prevails. After the disappointment of June’s match, Joshua will be looking to make amends on December 7th.

Will we see another shock to add to the history books?

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