The list of fighters who defeated Mike Tyson in his prime

In his prime, Mike Tyson was one of the most feared men on the planet. The former world heavyweight boxing champion was one of the most violent knockout artists that the sport of boxing has ever witnessed. However, even in his prime, some fighters shocked the world by defeating The Baddest Man on the Planet.

Mike Tyson's rapid reflexes and agility combined with the ferocious power in his hands made him a beast that very few were ever able to tame during his prime. He suffered the first loss of his professional career after 37 straight wins inside the ring.

Through the course of his legendary career, the 54-year-old picked up 50 wins and a total of just six losses.

Every time Mike Tyson was bested inside the boxing ring

Buster Douglas

Arguably, Mike Tyson's career's biggest upset occurred on February 11, 1990, in Tokyo, Japan, when he succumbed to a shocking defeat against overwhelming underdog Buster Douglas. Heading into the fight, Mike Tyson had a perfect 37-0 record and held the WBA, WBC, IBF, and lineal heavyweight titles.

To the shock of spectators around the world, Douglas knocked Tyson out in the 10th round of the fight to cause what is widely regarded as one of the biggest upsets in combat sports history.

While there were rumors that Tyson was going through a personal crisis heading into a fight, the upset was still big enough to send shockwaves through the world of boxing at the time.

Evander Holyfield

Mike Tyson had seemingly recovered from the loss against Douglas very well. Iron Mike picked up seven straight wins following the shock defeat that ended his undefeated streak. However, on November 9, 1996, Tyson faced Evander Holyfield at the MGM Grand Arena in Las Vegas.

The fight turned out to be a violent slugfest, as Holyfield started to pick Tyson apart in the later rounds. He managed to finish Tyson in the 11th round to pick up one of the biggest wins in heavyweight history.

Tyson wanted a quick turnaround to rematch Holyfield, and his demands were met. The pair squared off once again at the MGM Grand Arena on June 28, 1997. Mike Tyson looked good in the initial rounds and was on his way to picking up an impressive win in the rematch before Holyfield head-butted him.

An infuriated Tyson tried to land haymakers on his opponent but failed to do so. Instead, bit Holyfield's ear when they were caught in a hold. However, the fight continued until Tyson repeated the same actions, biting Holyfield's other ear from the clinch.

Tyson suffered a DQ loss in the third round and lost his boxing license. He was also fined $3,000,000 as a punishment for displaying unsportsmanlike conduct during the fight.

Lennox Lewis

While these were the three fights that Mike Tyson lost in his prime, he suffered three more losses towards the end of his career. He got knocked out in what was his last shot at the heavyweight title against Lennox Lewis on June 8, 2002. Tyson was 35 at the time and faced Lewis, who was in the best shape of his life.

Danny Williams and Kevin McBride

His other two defeats came against Danny Williams and Kevin McBride in 2004 and 2005, respectively. Mike Tyson faced Williams after a 17-month layoff and got knocked out in the fourth round of the fight after suffering a knee injury early on in the fight.

After the sixth round against McBride, he retired in what was the final fight of his career as a professional boxer.