What happened to man who ended Mike Tyson's undefeated record in one of the most shocking upsets in sports history

Mike Tyson saw his unblemished professional record ruined by an underdog - but what happened to him after the shock triumph?

Back in 1990, Mike Tyson was at his most dangerous, facing a routine fight to retain his WBA, WBC and IBF Heavyweight titles in Tokyo.

Billed as 'Tyson is back!', the fight in Tokyo saw the undefeated Tyson in a precursor bout to a likely heavyweight showdown with Evander Holyfield, who was ringside in Japan. He was expected to win comfortably, but opponent Buster Douglas had other ideas and what followed is now considered one of the biggest upsets in sports history.

Tyson entered the fight with a 37-0 record, the undisputed heavyweight champion and prominent commentators were predicting a 90-second contest in Tyson's favour. Yet Douglas - a 42-1 shot before the fight - began without fear and was not afraid to attack Tyson when he could.

Douglas shocked the world when he knocked out Mike Tyson in Tokyo. (Image: Getty)

Tyson took punishment throughout and barely survived the ninth round, and Douglas became the first fighter to knock Tyson out with a brutal uppercut in round ten followed by four punches to the head. The referee stopped the fight, making Douglas the new undisputed heavyweight champion and an instant overnight sensation.

However later that year, facing Holyfield, Douglas would last just three rounds and his fate was sealed, ending a whirlwind few months that saw him embroiled in a promotional battle between promoters Steve Wynn and Don King - the latter a partner of Donald Trump.

Evander Holyfield needed just three rounds to beat Douglas in Las Vegas. (Image: Getty)

As outlined by the Independent, Wynn secured Douglas on a two fight deal worth £43m, and he headed into the Holyfield bout in Las Vegas as 'the man that knocked out Tyson.' It is claimed Douglas enjoyed his fame and did not properly prepare for the Holyfield fight and was 14lbs heavier than he was against Tyson.

Douglas fell in round three and was criticised for his attitude in the build-up and retired after the fight. He would launch a brief comeback after health issues, although despite constant talk of a rematch with Tyson, his last fight would come in 1999 with his final record standing at 38-6-1. He won a reported $1.3m from the Tyson win and a further $24m from his Holyfield fight.

Mike Tyson on Buster Douglas

Tyson opened up about the defeat when he spoke on 'The Pivot' podcast three years ago.

When asked about what it felt like to lose for the first time, Tyson explained: "Whew. Relief. It happened. It’s over. Losing’s not that bad. Now I’m even a better fighter because I’m not afraid to lose."

He added: "Fighting Buster was one of the best things that ever happened to me.

“I was so stressed out being the champ. My hair was falling out. I was stressed out, but I was playing it out like I was a hard guy. Scared to death. Little kid and you’ve got the whole sport on your back. Everyone is trying to get your money and they’re trying to sue you.

“You know what Buster did for me and to the world? He made me human. I wasn’t an animal savage. It made me human and it made me a better fighter. Now, I’ll do things that I’d never do before, take chances.”