Throughout his illustrious professional boxing career, legendary fighter Mike Tyson has won 50 out of 58 matches. Of those victories, 44 opponents were knocked out by the powerful punches of “Iron Mike.” However, two of Tyson’s six defeats came at the hands of his compatriot Evander Holyfield.

Holyfield defeated Tyson in November 1996 to capture the WBA heavyweight title and successfully defended it seven months later when Tyson was disqualified for the infamous ear-biting incident.

When asked who the toughest opponent he ever faced was, Tyson said on his podcast: “It’s Holyfield. He’s a damn monster. I vividly remember the two fights where Holyfield beat me. It was terrible. He fought with incredible composure, a cool head, and his feet never stopped moving.”

Holyfield famously defeated Mike Tyson twice

Legendary Evander Holyfield is set to return to the ring after a long hiatus, facing Kevin McBride on June 5. However, before this bout, Holyfield has been entangled in negotiations for a multimillion-dollar fight with his old rival Mike Tyson.

Despite initial agreements, negotiations for a highly anticipated and lucrative bout between the two heavyweight legends ultimately fell through.

Revisiting the historic ear-biting incident, Tyson earned $30 million from that fight, despite it lasting only three rounds and ending controversially. After leaving the ring, “Iron Mike” spent $1.4 million in just 90 minutes.

First, he damaged his new Lamborghini by driving it recklessly. Frustrated and believing the car was cursed, Tyson handed the keys to a nearby security guard. Shortly afterward, he went on a shopping spree at a Versace store in Caesar’s Palace, racking up a bill of over $788,000.

Tyson’s wild spending and legendary fights remain a testament to his dramatic and storied career in the boxing world.