In 1988, Tyson became the lineal champion when he knocked out Michael Spinks in the first 91 seconds of the fight. Tyson successfully defended the world heavyweight championship nine times, including victories over Larry Holmes and Frank Bruno. Tyson lost his titles to 42-to-1 underdog James "Buster" Douglas on February 11, 1990, in Tokyo, Japan, by a knockout in round 10. Tyson continued in his quest to regain the titles, defeating Donovan Ruddock twice in 1991. Tyson was then scheduled to take on the undisputed heavyweight champion Evander Holyfield but pulled out due to injury.
In 1992, Tyson was convicted of raping Desiree Washington, for which he was sentenced to six years in prison but was released after serving three years. After being released from prison in 1995, he engaged in a series of comeback fights. In 1996, Tyson won the WBC and WBA titles after defeating Frank Bruno and Bruce Seldon by knockout. After being stripped of the WBC title, Tyson lost his WBA crown to Evander Holyfield in November, 1996 by an 11th round TKO. Their 1997 rematch ended when Tyson was disqualified for biting off part of Holyfield's ear.
In 1992, Tyson was convicted of raping Desiree Washington, for which he was sentenced to six years in prison but was released after serving three years. After being released from prison in 1995, he engaged in a series of comeback fights. In 1996, Tyson won the WBC and WBA titles after defeating Frank Bruno and Bruce Seldon by knockout. After being stripped of the WBC title, Tyson lost his WBA crown to Evander Holyfield in November, 1996 by an 11th round TKO. Their 1997 rematch ended when Tyson was disqualified for biting off part of Holyfield's ear.