Mike Tyson knocked out in sparring match with retired boxer who lost 17 fights before surprising defeat to Buster Douglas

In 1990, Mike Tyson faced one of boxing’s biggest upsets against James ‘Buster’ Douglas. Few believed Douglas could defeat Tyson, who was then undefeated at 37-0 and the reigning heavyweight champion. Motivated by his mother’s recent death, Douglas delivered a stunning performance, knocking out Tyson in the 10th round in Tokyo.

Before the fight, rumors suggested Tyson had been neglecting training, distracted by a planned bout with Evander Holyfield. During preparation, Tyson was knocked down by sparring partner Greg Page, hinting at trouble. Footage showed Page landing a right hand that floored Tyson, though some dismissed it as a slip.

Despite this setback, Tyson continued sparring with Page but seemed unfocused, reportedly quitting early during sessions. Page, a skilled boxer and former WBA champion, had a notable career with a record of 58-17-1, including wins over former champions.

Page again challenged Tyson a year later, causing a significant cut over Tyson’s eye before a fight with Alex Stewart. This injury required 48 stitches and delayed the match by three months. Tyson eventually defeated Stewart in a first-round knockout and secured victories over Donovan Ruddock, becoming the top contender to face Holyfield.

However, Tyson’s career took a turn when he was convicted of rape, delaying the anticipated fight with Holyfield. Upon his return to boxing, Tyson regained the WBA title by defeating Bruce Seldon, setting up the long-awaited clash with Holyfield in 1996. In another upset, Holyfield outboxed Tyson, winning the title. Their infamous rematch in 1997 ended in controversy when Tyson was disqualified for biting Holyfield’s ear.