Which was Mike Tyson's first loss? Revisiting the downfall of the boxing legend

Mike Tyson's first loss came in 1990 in one of the biggest upsets of all time.

'Iron Mike' famously became heavyweight champion in 1986, at just 20 years old. Scoring a knockout win over Trevor Berbick, he made history as the youngest heavyweight titleholder ever. Instantly, he became one of the biggest sports figures on the planet.

Over the coming years, he would defeat names such as Larry Holmes, Michael Spinks, Frank Bruno, and more. That was supposed to lead to a 1990 clash with Evander Holyfield. However, before he could face 'The Real Deal', he had to fight James 'Buster' Douglas.

Mike Tyson entered that matchup in Toyko an astronomical 42 to 1 betting favorite. The fight was viewed as nothing more than a warm-up for his future bout with Holyfield. However, early, it was clear that Douglas was ready to make the most of his opportunity.

'Buster' used his reach and jab to win some early rounds of the contest. Eventually, Douglas began to dominate, but Tyson returned fire in the eighth round. There, the heavyweight champion got a knockdown, with the challenger barely beating the count.

James Douglas beat the count and eventually scored a tenth-round knockout of his own. Over three decades later, the upset is still arguably the biggest in boxing history.

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Did Mike Tyson rematch James 'Buster' Douglas?

Unfortunately for fans, there was never a rematch between Mike Tyson and James 'Buster' Douglas. Despite the monumental significance of Tyson's first loss, he never held the ring with Douglas again.

The reason is that the former heavyweight champion didn't have a mandatory rematch clause in his contract. While that is standard today, that wasn't the case in 1990. Whenever Tyson lost, they had no legal recourse for them to take.

However, there was still talk of a rematch between Mike Tyson and 'Buster'. Sadly, Don King failed to strike a deal with the newly crowned champion, so he instead faced Evander Holyfield. 'The Real Deal' famously won the title with ease later that year in October.

It was only after that fight, that 'Iron Mike' got to finally face Holyfield. Even then, their clash was delayed years due to Tyson's prison sentence. However, when the two heavyweight legends did meet in the ring, it produced one of the greatest rivalries in the sport's history.