In the mid-to-late 1980’s boxing legend Mike Tyson fully lived up to his reputation as ‘The Baddest Man On The Planet,’ but just two months into 1990’s his perfect 37-0 record came to a screeching halt as Buster Douglas KO’d him in one of boxing’s biggest ever upsets.
Up until that point Tyson had never even been dropped in the ring – or at least not in competition. However, in sparring it was a different story as this video shows.

Tyson’s fight with Douglas took place in Tokyo, Japan on February 22nd of 1990, and this public sparring session occurred less than three weeks prior to the event.
’Iron Mike’s’ sparring partner on this occasion was Greg Page, who’d briefly held the WBA heavyweight title in 1984. However, Page had suffered a significant number of losses after that, including to the aforementioned Douglas in 1986.
It was a turbulent time in Tyson’s life, despite being at the peak of his fame and holding the WBC, WBA, IBF and ‘The Ring’ heavyweight titles, and he’d become as notorious outside of the ring as in it.
His personal life was in turmoil, having divorced Robin Givens in the summer of 1989 following only 11 months of marriage, while he’d also ditched his manager Bill Cayton after a messy legal wrangle involving Don King, and fired his long-time coach Kevin Rooney.
Together with the fact that he’d become a party animal and was spending money hand over fist, it was inevitable that all this chaos would catch up with him sooner rather than later.
The warning signs were clearly there when Page floored Tyson with a short right hook, bringing an abrupt end to sparring that day as the world’s media watched.
After that the word was that Tyson continued to look lethargic in training, but still few really believed that the massive underdog, Douglas was the man to beat him.
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However, that’s exactly what happened, with Douglas leaving Tyson sagging against the ropes with a straight right in the tenth round after a series of punches beforehand had stunned the champion.
Tyson sat dazed on the mat for a few seconds before struggling to his feet on unsteady legs, but he was clearly still rocked and the referee waved off the fight, bringing a disappointing end to his unbeaten reign of terror in the heavyweight division.





