Mike Tyson and Evander Holyfield have shared the boxing ring twice. It was 'The Real Deal' who emerged victorious on both occasions. The pair of former heavyweight champions first collided in 1996. ... Ending Mike Tyson's eight-fight win streak, Holyfield sent shockwaves around the world of boxing.

How many times did Tyson fight Evander?

2. Evander Holyfield - The only boxer to beat Mike Tyson twice. Mike Tyson did bounce back from the loss to Douglas with two wins over Henry Tillman and Alex Stewart, followed by a bout with No.

Who won Tyson vs Holyfield 1?

Tyson and Holyfield had an iconic rivalry in the 1990s. Holyfield won the first fight in November 1996 via an 11th round TKO. In the June 1997 rematch, Tyson earned a 4th round disqualification after biting Holyfield's ear twice.