In 1990, Mike Tyson suffered one of the most shocking losses in boxing history to James ‘Buster’ Douglas.

Few believed the Ohioan had a chance of beating ‘Iron Mike’, who then had a 37-0 record and was the reigning world heavyweight champion. But Douglas, motivated by the death of his mother 23 days before the fight, gave the performance of a lifetime when he knocked out Tyson in the 10th round before a stunned crowd at the Tokyo Dome.

Reports suggested that Tyson had been negligent in training and had overlooked Douglas, who had signed to fight Evander Holyfield that summer in Atlantic City. The reality was predicted when Tyson was defeated by his long-time training partner Greg Page just before the fight. Footage from a Japanese television channel shows Tyson and Page fighting in the gym in front of the media. As Tyson rushed in with a left hook, he was hit by Page with a right hand that sent him to the floor.

Tyson quickly stood up and dusted himself off, but the sparring session was cut short.  Former super lightweight world champion Tauyoshi Hamada, who watched the two fighters exchange blows from outside the ring, commented: “It was clearly a fall. I saw it at the gym and also saw it on television.” picture. It was a right hook from close range.” However, a trainer at the gym described the action as ‘sliding or pushing’.

A report from the New York Times said Tyson fought Page again the next day but “gave up after three rounds” and decided to take a day off. Page was a skilled boxer and held the WBA heavyweight championship from 1984 to 1985. During a 23-year professional career, Page posted a record of 58-17-1, including wins over previous world champions Tim Witherspoon, James ‘Bonecrusher’ Smith and Gerrie Coetzee. Page made headlines again a year later when he cut a deep gash above Tyson’s right eye just over two weeks before his fight with Alex Stewart.

The injury was caused by a head collision during a workout at the Trump Plaza Hotel and Casino in Atlantic City. Tyson needed 48 stitches to close the cut and the fight with Stewart was postponed for three months. Tyson won his final fight by knocking out his opponent in the first round and quickly followed up his victory with two victories over Donovan Ruddock. By defeating Ruddock, Tyson became the number one contender to face Holyfield. But the fight once again failed after Tyson was convicted of raping Desiree Washington and sentenced to six years in prison.

When ‘Iron Mike’ finally returned to the boxing ring, the super fight took place. After regaining the WBA title by defeating Bruce Seldon, the Tyson vs Holyfield fight finally took place in 1996.nHowever, in an unexpected turn of events, ‘The Real Deal’ defeated Tyson and prevented him from winning the championship belt.

When the pair fought again in 1997, things turned ugly when Tyson bit Holyfield’s ear and was disqualified.