On February 11, 1990, dealing with the flu and the death of his mother just weeks before the fight, Buster Douglas defeated heavyweight champion Mike Tyson. Tyson was 37-0 before this loss. It ranks among the biggest upsets in sports history as Douglas was a 42-to-1 underdog.

Douglas remained the world heavyweight champion for eight months before losing to Evander Holyfield.

He ended his career with a 38-6 record. He is now 59-years-old.

Credit: ESPN via YouTube