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How One Mike Tyson Fight Redefined the Meaning of an Upset – When Sports History Was Rewritten

July 9, 2025
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Mike Tyson makes history with wins of losses. On February 11, 1990, the boxing world learned a lesson it would never forget: never assume the ending before the bell rings. The stage was set in Tokyo, where Mike Tyson, the undefeated and undisputed heavyweight champion, was expected to breeze through another challenger. Buster Douglas, meanwhile, was cast as the designated fall guy – so much so that Las Vegas bookmakers gave him 42-to-1 odds.

Buster Douglas and Mike Tyson

Some casinos didn’t even bother to take bets on Tyson, figuring it would be easier to sell ice to penguins. Mike Tyson’s reputation at the time was nearly mythic. He had knocked out his first 19 opponents, most of them before the crowd even had time to settle in. The world waited for another quick demolition, and Tyson’s next big payday against Evander Holyfield was already being penciled in.

Douglas, by contrast, was seen as a warm-up act – a solid pro, but not the sort who rewrites history. But boxing, like life, has a way of ignoring the script. Douglas entered the ring carrying the weight of his mother’s recent passing. Some say that loss gave him a new sense of purpose. Whatever the reason, he fought with a determination that surprised everyone – except maybe himself.

The fight itself was a slow burn. Douglas was knocked down in the eighth round but got up, dusted himself off, and went back to work. By the tenth, he had Tyson reeling. A crisp uppercut and a flurry of punches sent the “Baddest Man on the Planet” to the canvas for the first time in his career. Mike Tyson, dazed, fumbled for his mouthpiece as the referee counted him out. The Tokyo Dome crowd of 40,000 sat in stunned silence. Around the world, jaws dropped.Commentators and fans struggled to process what they’d seen.

Image: @netflix/X

HBO’s Jim Lampley, recalling the moment years later, said he delivered the news as plainly as possible: “Mike Tyson has been knocked out.” No need for theatrics – reality had already done the heavy lifting. In an interview with Joe Rogan, Lampley recalled:

“The very first live fight I ever attended was the biggest upset in boxing history. And now here in front of me, 12, 14 feet away, is the result that’s going to supplant that as the biggest upset in boxing history. Mike Tyson has been knocked out. In about that tone of voice. I wanted to make it as matter-of-fact as possible because there was nothing I could do to elevate it by screaming or shouting… It was what it was. Right. Mike Tyson has been knocked out.”

Even Tyson, with the benefit of hindsight, admitted that Douglas was simply better that night and that the loss “made me human.”In the end, Douglas’s victory shook up boxing and the entire sports world.



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