Buster Douglas Knocks Out ‘Iron’ Mike Tyson – 1990:
There’s no denying that Andy Ruiz Jr.’s knockout of Anthony Joshua was a shocking spectacle to say the least. However, there’s just not another boxing upset that could top this one. Mike Tyson met Buster Douglas, in Tokyo on February 11, 1990. ‘Iron’ Mike was unbeaten and a feared a boxer as there ever was. He had dominated the heavyweight division for three years prior. His fight with Douglas was largely thought of as a mere setup fight for a showdown with the also-undefeated Evander Holyfield.
So no one gave 42-to-1 dog Douglas much of a chance. How could they have, really? Douglas controlled the action from the outset, peppering Tyson with endless jabs. The strikes took their toll and Tyson’s eye began to sell shut, something his corner was not prepared for. Tyson knocked Douglas down in the eighth round, but Douglas came back. He landed a ton of damage in the ninth round and Tyson was in trouble heading into the tenth. A monster uppercut rocked Tyson, and a four-punch combo sealed the deal for the biggest upset in boxing history.