Mike Tyson, one of boxing’s most intimidating and ferocious champions, is no stranger to tough fights. But there is one bout in his storied career that stands out—an encounter that left a lasting impact on the heavyweight legend, making him hesitant to return to the ring. That fight was against the formidable Buster Douglas in 1990.

Coming into the bout, Tyson was the undisputed champion, with an aura of invincibility surrounding him. He had amassed a record of 37-0, with 33 of those wins coming by knockout. Many viewed him as unbeatable, and his fights were often over before they began, thanks to his fierce punches and aggressive style. However, Buster Douglas, seen as a significant underdog, shocked the world when he faced Tyson in Tokyo.

Douglas delivered a performance that would go down in boxing history, using a combination of precise jabs, counterpunches, and solid defense. Tyson, who seemed underprepared for the challenge, struggled to maintain his usual dominance. In the tenth round, Douglas landed a devastating uppercut, followed by a barrage of punches that sent Tyson to the canvas. It was the first time the world had seen Tyson defeated so decisively.

This loss changed the trajectory of Tyson’s career. Many believe that it marked the beginning of his decline as a fighter, introducing doubts that lingered over his subsequent matches. While he returned to the ring multiple times after that defeat, his aura of invincibility had been shattered.

Tyson later spoke about the fight, acknowledging that he underestimated Douglas and wasn’t in the best physical or mental shape. The defeat haunted him for years, serving as a stark reminder that even the greatest can fall. The fight against Buster Douglas remains one of the most shocking upsets in boxing history, a moment that redefined Tyson’s legacy and left an indelible mark on the sport.