Mike Tyson recently made a return to the boxing ring in a match with Roy Jones Jr. on November 28, 2020. The much-anticipated bout ended in a draw, but fans from around the world tuned in to catch Iron Mike inside the ring after 15 years away.

During the long tenure of his career, Mike Tyson has slept several opponents with his vicious hooks. But he himself has suffered a similar fate a total of 6 times at the hands of 5 fighters.

We have taken the liberty of listing them all here.

1. James ‘Buster’ Douglas – The first boxer to defeat Mike Tyson

Mike Tyson faced Buster Douglas on February 11, 1990 amid heaps of personal turmoil, including a separation and divorce with Robin Givens. Tyson had also let go of his trusted manager Bill Cayton and longtime trainer Kevin Rooney.

There were reports of Mike Tyson putting in less than 100% effort in training ahead of the boxing match. Buster Douglas showed up with quicker jabs and made the most of his 12-inch reach advantage over Tyson.

The eighth round did see Tyson knock Douglas to the floor, but the latter recovered in time. It was questioned later whether the referee gave him longer than usual to get up from the floor. In any case, Douglas’ quick moves and back-to-back jabs proved too much for Tyson in the next two rounds.

Iron Mike was sent crashing to the mat for the first time ever after an uppercut followed by a four-punch hook combination in the tenth round. Tyson was counted out by referee Octavio Meyran, giving him the first loss of his career.

With little to no bets in favor of Douglas, Mike Tyson’s first loss is considered to be one of the biggest upsets in sports history.

Tyson later said that he needed that loss to bring him back to reality and give him a better worldview.

“I needed that fight to make me a better person and fighter. I have a broader perspective of myself and boxing.”

Watch the video of the knockout below:

2. Evander Holyfield – The only boxer to beat Mike Tyson twice

Fight 1

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. 2 contender Donovan “Razor” Ruddock, one of the scariest heavyweight boxers at the time.

The win set him up for a contest with Evander Holyfield, but Tyson had to withdraw because of a rib cartilage injury. The two could ‘finally’ met after Mike Tyson had served his prison sentence, in a title bout named Finally. Holyfield was retired by then, but returned as an underdog for the match.

They faced each other on November 9, 1996, and Evander Holyfield became the second boxer to knock Mike Tyson out when the match ended by referee’s stoppage in round 11.

Fight 2

Mike Tyson and Evander Holyfield met again a few months later on June 28, 1997. In a match named The Sound and the Fury, held at the same venue as the first one – MGM Grand Garden Arena – the two made history by earning the highest fight purses in boxing.

But the fight ended in a controversial disqualification, as Mike Tyson infamously went on to bite Holyfield’s ears twice during the match. Points were deducted the first time, but the bite was severe enough to tear off parts of Holyfield’s ear. The second time it happened, referee Mills Lane stopped the match and Holyfield won via disqualification – the first boxing bout in over 50 years to end in such a way.

A riot subsequently broke out among the audience, injuring several people. Tyson later apologized and his license to box in USA was temporarily invoked by NSAC.

3. Lennox Lewis

Tyson and Lennox Lewis had a heated rivalry leading up to their bout. The entourages of the two boxers engaged in a brawl at the promotional press conference. The fight was initially set to be in Nevada, but NSAC denied Mike Tyson a license because of the sexual assault charges against him. Several other states followed suit.

The fight was finalized for June 8, 2002, at Pyramid Arena, Memphis, Tennessee. Lennox Lewis dominated and he knocked Tyson out in the eighth round of the bout. At that time, the fight was the highest-grossing PPV event in history. Unlike some other times, Mike Tyson was respectful towards his opponent after this loss and even went on to praise Lennox’s game.

4. Danny Williams

After Lewis, Mike Tyson faced Clifford Etienne and beat him in 49 seconds in what would be his last professional victory inside the ring. During this fight, Tyson’s personal life had already started to deteriorate at a fast pace. In 2003, he announced bankruptcy.

Iron Mike tried to make a comeback against Danny Williams on July 30, 2004 after a period where rumors of a fight with Bob Sapp were constant. That never happened, and Mike Tyson faced Williams instead, once again in a losing effort.

Tyson was in his element for the first couple of rounds, and was unexpectedly knocked out in the fourth. it was later revealed that Mike Tyson had a torn ligament in one knee and was basically fighting on one leg.

5. Kevin McBride

Mike Tyson’s last professional fight ended in an abrupt and unceremonious way, which was not at all fitting of the great boxer and his illustrious career. Facing McBride on June 11, 2005, Mike Tyson quit before the start of the seventh round, stunning the crowd and everyone watching from home.

In his documentary, Mike Tyson later revealed that he fought McBride for the fight purse and did not expect to win. After this fight, Mike Tyson retired from professional boxing.

4. Danny Williams

After Lewis, Mike Tyson faced Clifford Etienne and beat him in 49 seconds in what would be his last professional victory inside the ring. During this fight, Tyson’s personal life had already started to deteriorate at a fast pace. In 2003, he announced bankruptcy.

Iron Mike tried to make a comeback against Danny Williams on July 30, 2004 after a period where rumors of a fight with Bob Sapp were constant. That never happened, and Mike Tyson faced Williams instead, once again in a losing effort.

A riot subsequently broke out among the audience, injuring several people. Tyson later apologized and his license to box in USA was temporarily invoked by NSAC.

They faced each other on November 9, 1996, and Evander Holyfield became the second boxer to knock Mike Tyson out when the match ended by referee’s stoppage in round 11.

Fight 2

Mike Tyson and Evander Holyfield met again a few months later on June 28, 1997. In a match named The Sound and the Fury, held at the same venue as the first one – MGM Grand Garden Arena – the two made history by earning the highest fight purses in boxing.

They faced each other on November 9, 1996, and Evander Holyfield became the second boxer to knock Mike Tyson out when the match ended by referee’s stoppage in round 11.

Fight 2

Mike Tyson and Evander Holyfield met again a few months later on June 28, 1997. In a match named The Sound and the Fury, held at the same venue as the first one – MGM Grand Garden Arena – the two made history by earning the highest fight purses in boxing.

During the long tenure of his career, Mike Tyson has slept several opponents with his vicious hooks. But he himself has suffered a similar fate a total of 6 times at the hands of 5 fighters.

We have taken the liberty of listing them all here.

1. James ‘Buster’ Douglas – The first boxer to defeat Mike Tyson

Mike Tyson faced Buster Douglas on February 11, 1990 amid heaps of personal turmoil, including a separation and divorce with Robin Givens. Tyson had also let go of his trusted manager Bill Cayton and longtime trainer Kevin Rooney.