Douglas had already been fighting since the early 1980s, but there was nothing in his record that suggested that he was capable of handing Tyson his first loss. In fact, bookmakers made him a 42-1 underdog for the Feburary 10, 1990, fight in Tokyo, Japan. Douglas surprised the world by dominating the fight from the beginning, seemingly hitting Tyson at will with jabs and right hands and getting out of range when Tyson launched his own punches. Only in the 8th round did Tyson come close to victory. In the waning seconds of the round Mike Tyson hit Buster with an uppercut and down went Douglas. He was up at the count of 8, and the bell rang before Tyson could follow up on his sudden success. After the fight Tyson and his team would protest that the referee had started his count too late and that Douglas should have been counted out, but those protest were of no avail. In the 10th round, a devastating combination from Douglas floored Tyson for the first time in his boxing career. When Tyson failed to climb to his feet on time, the fight was over. For that upset, the public reaction could be typified with a cover of Sports Illustrated Magazine with his picture and the text, "Rocky Lives!" in allusion to the movie boxing hero who also defeated his champion opponent against all odds.

Douglas couldn't follow up on that success, however. In the following months he did little training and his weight ballooned. When he defended the title later in the year against Evander Holyfield, he was nowhere near the fighter he was when he had beaten Tyson. Holyfield knocked him out in three rounds and Douglas retired from boxing afterwards. A couple of years later he made a comeback. He was successful at first, but when unheralded Lou Savarese knocked him out in the first round he hung up his gloves for good.

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