Mike Tyson's only match against Evander Holyfield was in 1990.
Mike Tyson . Attempting to regain the titles , Tyson defeated Donovan Ruddock twice in 1991 , but pulled out of a fight with then-undisputed heavyweight champion Evander Holyfield ( who had defeated Douglas later in 1990 ) due to a rib injury . After being stripped of the WBC title in the same year , Tyson lost the WBA title to Evander Holyfield by an eleventh-round stoppage . Their infamous 1997 rematch ended when Tyson was disqualified for biting Holyfield 's ears .