Douglas provided one of the biggest boxing upsets ever upsets by knocking out Tyson, who partied with two dozen girls just days before the fight

Talented singer Bobby Brown has revealed he and Mike Tyson partied with two dozen girls before the boxing legend’s shock loss to Buster Douglas.

Douglas was a 42-1 underdog against then-unbeaten heavyweight champion Tyson. Fans considered Douglas as a warm-up fight for Tyson as he prepared to fight his soon-to-be rival Evander Holyfield, but it proved to be anything but.

Tyson’s left eye was visibly swollen by the eighth round of the fight, as he floored Douglas for the first time in the bout with a trademark uppercut. Douglas refused to give up and knocked Tyson down with a flurry in the 10th round, leaving him unable to beat the count.

The fight is regarded as one of the biggest upsets in boxing history. Tyson’s longtime friend Brown has now revealed that he partied “really hard” with ‘Iron Mike’ in the lead up to the historic title fight.

“We used to do crazy sh**,” Brown said in an interview for the A and E documentary. “Me and Mike Tyson are friends to this day, but there was a time when we partied in Japan right before his fight with Buster Douglas. We partied like really, really, really hard.

“There must have been two dozen girls in the room with me and Mike, we partied. I was trying to tell him to get some sleep.” Brown then joked: “Eventually he got some sleep [in the ring]! Do not put that part in there please, he is going to kill me.”

Tyson never did get the chance to avenge his loss to Douglas, as the underdog went on to fight Holyfield in his next fight and lose his heavyweight belts. Tyson went on to win world titles against Frank Bruno and Bruce Seldon later in his career, but Douglas never challenged for a world title again.

Buster Douglas knocked out Mike Tyson in 1990 ( Image: Sports Illustrated via Getty Images)

‘Iron Mike’ made his boxing return in 2020 after 15 years away from the ring, going the distance in an exhibition fight against fellow boxing legend Roy Jones Jr. Tyson has been backed to fight Jake Paul next and admitted he recently opened talks with the YouTube star over their $300million clash.

Paul’s move from internet fame to boxing has been criticised by purists, but his good friend Tyson has recently come to his defence. “He’s a fighter but they don’t want to credit him as being a fighter. He can fight and everybody wants to kick his a** because he p***** everybody off. He’s a great salesman and promoter,” Tyson said on the Club Random Podcast.