Almost everyone assumed that Douglas' fight versus Mike Tyson was going to be another quick knockout for the champion. Only one betting parlor in Las Vegas would hold odds for the bout, and many thought it was just an easy tune-up for Tyson before a future mega-fight with undefeated cruiserweight champion Evander Holyfield (who was ringside for the event).

Douglas' mother, Lula Pearl, died 23 days before the title bout.^[1] Douglas, who had trained hard, surprised the world by dominating the fight from the beginning, utilizing his 12-inch reach advantage to perfection. He seemingly hit Tyson at will with powerful jabs and right hands and skillfully danced out of range of Tyson's own punches. The champion had not taken Douglas seriously, expecting another quick and easy knockout victory. He was slow, refusing to move his head and slip his way in (his usual effective strategy) but rather setting his feet and throwing big, lunging hooks, repeatedly trying to beat Douglas with single punches. By the fifth round, Tyson's left eye was swelling shut from Douglas' many right hands, and ringside HBO announcers proclaimed it was the most punishment they had ever seen the champion absorb.

Tyson's cornermen appeared to be unprepared for the suddenly dire situation. They had not brought an endswell to the fight, so they were forced to put ice water into a latex glove to hold over Tyson's swelling eye. By the end of the fight, Tyson's eye had swollen almost completely shut. In the eighth round, Tyson landed a right uppercut that knocked Douglas down. The referee's count engendered controversy as Douglas was on his feet when the referee reached nine, although the official knockdown timekeeper was two seconds ahead. However, a comparison with Douglas's winning knockdown count issued to Tyson two rounds later revealed that both fighters had received long counts.

Tyson came out aggressively in the ninth round and continued his attempts to end the fight with one big punch. Douglas continued to utilize his strategy and held Tyson at bay with his jab. Douglas dominated the tenth round from the outset. Douglas scored a huge uppercut, followed by a rapid combination, and knocked Tyson down for the first time in his career, making boxing history. Tyson struggled to his knees and picked up his mouthpiece lying on the mat next to him. He awkwardly attempted to place it back into his mouth. The image of Tyson with the mouthpiece hanging crookedly from his lips would become an enduring image from the fight. He was unable to beat the referee's count, and Douglas was the new heavyweight champion of the world.

While still Champion, Douglas appeared on the February 23, 1990 episode of the World Wrestling Federation's "WWF The Main Event", as special guest referee for a rematch between Hulk Hogan and Randy "Macho Man" Savage. Originally, Mike Tyson was scheduled to be the guest referee, but following the upset, the WWF scrambled to sign on Douglas for the event. At the end of the match, Douglas was provoked into a 'storyline' punch and knockout of Savage, who was the 'heel' wrestler in the match.

Douglas made his only defense of the heavyweight title on October 25, 1990, against Evander Holyfield. Douglas came in the fight heavy, at 246 lbs (over 15 pounds heavier than in his fight against Tyson). In the third round, Douglas loaded up with a right uppercut that Holyfield easily countered with a straight right that knocked Douglas down and out for the full count. Douglas decided to retire after the fight.

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