Tyson and Bruno fought twice. The first fight took place at Las Vegas Nevada on February 25, 1989 instead of the initial setup of September 3, 1988.

Bruno vs Tyson, was originally scheduled for September 3, 1988, at Wembley Stadium in London, England. However all plans went up in the air after Tyson sued to break his contract with his manager Bill Cayton, who was served with papers on June 27 1988, the night Tyson knocked out Michael Spinks. Tyson and Cayton settled out of court on July 26, after which Tyson said he wanted "six to eight weeks off" before the fight with Bruno.

On the day of the fight, Tyson was all hyped up and would eventually knock Bruno down in round five. Tyson then went on to fight a few more opponents before losing to Buster Douglas in Tokyo in 1991. He then got jailed for a rape charge and served a four years prison sentence.

He got back on his feet after his release from prison and set up a second fight with Bruno on March 16, 1996 at the MGM Grand Arena in Paradise, Nevada. On the day of the fight, Tyson was all hyped up as he entered the ring with a theme song from Tupac Shakur a famous rapper and friend of Tyson at the time. The fight would only last three rounds as Tyson came out victorious once again.

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