Mike Tyson, the iconic 'Iron Mike,' suffered his first loss in 1990, marking one of the biggest upsets in the history of boxing.

In 1986, Tyson made headlines by becoming the heavyweight champion at just 20 years old. His knockout victory over Trevor Berbick earned him the distinction of being the youngest heavyweight titleholder ever (though not yet undisputed), catapulting him into superstardom as one of the most prominent sports figures worldwide.

Over the following years, Tyson secured victories against notable opponents such as Larry Holmes, Michael Spinks, Frank Bruno, and many others. These triumphs were expected to lead to a highly anticipated showdown with Evander Holyfield in 1990. However, before Tyson could face 'The Real Deal,' he had to contend with James 'Buster' Douglas.

Mike Tyson entered the Tokyo matchup as an astonishing 42-to-1 betting favorite. The fight was initially viewed as a mere warm-up for his future battle with Holyfield. However, it became apparent early on that Douglas was determined to seize his moment.

'Buster' effectively utilized his reach and jab, winning several early rounds. As the contest progressed, Douglas continued to dominate, although Tyson mounted a comeback in the eighth round. It was in this round that the heavyweight champion scored a knockdown, with Douglas narrowly beating the count.

Despite Tyson's knockdown, James Douglas persevered and secured a tenth-round knockout of his own. To this day, this upset remains arguably the most significant in the history of boxing and perhaps all of sports.

Many fans wondered whether Mike Tyson and 'Buster' Douglas would have a rematch. Unfortunately, such a rematch never materialized because Tyson's contract did not include a mandatory rematch clause, a standard provision today that was absent in 1990. Consequently, there was no legal recourse for a rematch after Tyson's loss.

Nonetheless, discussions surrounding a potential rematch between Mike Tyson and 'Buster' Douglas persisted. Regrettably, a deal was never reached between Don King and the newly crowned champion. Instead, Douglas faced Evander Holyfield, who effortlessly claimed the title later that same year in October.

It was only after Holyfield's victory that 'Iron Mike' finally had the opportunity to square off against Holyfield in the ring. Despite being delayed due to Tyson's prison sentence, their eventual meeting in 1997 gave rise to one of the sport's most legendary rivalries.

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