The heavyweight legend headed into the bout in Tokyo on the back of 37 consecutive wins and was massive favourite to demolish his opposite corner.
Against all the odds, Douglas stunned the boxing world by putting Tyson to the canvas for the first time in his career in the tenth round.
It was regarded as one of the biggest shocks in sport history as Douglas snatched Tyson’s heavyweight belts.
Tyson was so confident that he would brush Douglas aside, he barely trained for the bout and instead was more interested in women.
In his autobiography, he wrote: “On January 8, 1990, I got aboard a plane to fly to Tokyo.
“Kicking and screaming. I didn’t want to fight; all I was interested in then was partying and f***ing women.
“I didn’t consider Buster Douglas much of a challenge. I didn’t even bother watching any of his fights on video.
“I had easily beaten everybody who had knocked him out.
“Besides having sex with the maids, I was seeing this young Japanese girl who I had had sex with the last time I was in Japan.
“Robin [his wife] would go out shopping and I would go downstairs to the back of the hotel where this young girl had a room… So that was my training for Douglas.
“The day before the fight I also had two maids at the same time. And then two more girls, one at a time, the night before the fight.”
Tyson would later admit that his shock defeat was a huge wake up call in his career.
He said: “I needed that fight to make me a better person and fighter. I have a broader perspective of myself and boxing.”
Tyson would bounce back with eight straight wins including claiming back his WBC and WBA heavyweight titles after knocking out Frank Bruno and Bruce Seldon.
Floyd Mayweather Says He’s Ready to Fight 50 Cent: ‘I Don’t Care About Weight Class’
During an appearance on Radio.com and V-103’s The Morning Culture last week, 50 said he would get in the ring with Mayweather, but felt like it would all depend on whether he would agree to an openweight bout. “I’d fight Floyd,” he said. “I don’t think I could make weight though. … Or he’d just have to let me not get down to 150. I tried I looked like a homeless person. I could make it down to probably, like 180.”
Mayweather took to Instagram Wednesday to not only respond to 50’s challenge, but also suggest scheduling this exhibition match for later this year. “I also heard that 50 cent would fight me but claims I’m too small. If he wants to lace up at the end of the year, we can do an exhibition then,” Floyd said. “I don’t care about weight class with any of these guys.”
Mayweather was scheduled to fight Logan Paul later this month but the bout was postponed. If Paul’s brother Jake defeats UFC fighter Ben Askren in their April boxing match, Floyd will get in the ring with him next, followed by 50. However, if 50 really wants to throw hands with Mayweather, he will need to agree that every cent of the prize money goes to the winner.
Shortly after Mayweather said he was willing to fight 50, the rapper took to IG to walk back his challenge.
“The fight is off because Floyd cant read 2 paragraphs of my New York Times best seller (Hustle Harder Hustle Smarter) on IG live.” 50 wrote.