Tyson-Ruddock happened on March 18, 1991. The fight received much attention and at the time was one of the biggest pay-per-view fights to date. The fight was brutal with Tyson scoring a knockdown in round 2 and then knocking Ruddock down toward the end of round 3. The fight went back and forth with Ruddock showing incredible heart and determination. Ruddock had his big moment in round 6 after connecting with some big shots and an uppercut that stunned Tyson before the bell sounded. Tyson started Round 7 charging at Ruddock and after catching him with numerous big shots. Referee Richard Steele controversially stopped the fight even though it appeared Ruddock, although staggering, was healthy enough to continue. The premature stoppage caused tempers to boil over with people angry at the decision.

After such a controversial first meeting, a rematch was called for. The second Tyson-Ruddock fight took place on June 28, 1991. The rematch went the distance, a full 12 rounds. Tyson knocked Ruddock down twice during the bout, and won by unanimous decision. The severity of the struggle was evident on both fighters after the fight: Ruddock had a broken jaw and Tyson suffered a perforated eardrum. Sports Illustrated reported that Ruddock's jaw may have been broken as early as the fourth round.Tyson was magnanimous after his triumph, praising Ruddock as a great heavyweight: 'Man this guy is tough, he'll be champion of the world one day if he stays dedicated and doesn't slip up'