In 1990, Mike Tyson faced one of the most shocking upsets in boxing history when he was defeated by James ‘Buster’ Douglas. The fight, held at the Tokyo Dome, saw Tyson, who was 37-0 and the reigning undisputed heavyweight champion, knocked out in the 10th round by Douglas, who was driven by the recent death of his mother.

Reports suggested that Tyson had not been training seriously and was already looking ahead to a future fight with Evander Holyfield, scheduled for that summer in Atlantic City. These reports seemed to be confirmed when Tyson was knocked down in a sparring session by his long-time training partner, Greg Page, just weeks before the bout.

Footage from a Japanese television network captured the moment Tyson was floored by Page during an open sparring session. As Tyson lunged in with a left hook, he was caught by a clubbing right hand from Page, sending him to the canvas. Although Tyson quickly got up and brushed himself off, the session was cut short.

Former super-lightweight world champion Tauyoshi Hamada, who was ringside, confirmed the knockdown: “It was clearly a down. I watched it at the gym and also saw it on television. It was a right hook from short range.”

However, some in the gym described the incident as a “slip or push.” Despite this, the New York Times reported that Tyson sparred with Page again the next day but quit after three rounds and decided to take the day off.

At the time of the sparring session, Page had a record of 30-8 and was preparing for a fight with Martis Fleming. Page, a former WBA heavyweight champion, had a respectable career with notable wins against former world champions Tim Witherspoon, James ‘Bonecrusher’ Smith, and Gerrie Coetzee. He ended his career with a record of 58-17-1.

Page made headlines again the following year when he opened a deep cut above Tyson’s right eye during a sparring session, just over two weeks before Tyson’s fight with Alex Stewart. The cut required 48 stitches and caused the fight to be postponed by three months.

The defeat to Douglas was a major turning point in Tyson’s career. Despite a brief resurgence, including victories over Donovan Ruddock, Tyson’s career never fully recovered. His planned fight with Holyfield was postponed after Tyson was convicted of rape and sentenced to six years in prison.

When Tyson returned to boxing, he finally faced Holyfield in 1996. In a significant upset, Holyfield outboxed and stopped Tyson to take his belt. Their infamous rematch in 1997 saw Tyson disqualified for biting Holyfield’s ear, marking a further decline in Tyson’s career. Tyson never won another world title after these events.