Mike Tyson’s Worst Defeats

Mike Tyson is often regarded as one of the most ferocious boxers in the history of the sport. His journey from a troubled youth on the streets of Brooklyn to the youngest heavyweight champion of the world at 20 years old, is nothing short of legendary. And on his way to the top, there were plenty of eye-catching moments. 

His second-round TKO of Trevor Berbick to become champion, his vicious knockout of Larry Holmes to earn redemption for his hero Muhammad Ali, and his fifth-round stoppage of British star Frank Bruno all spring to mind as some of his finest hours. However, for every impressive victory, there has been an even more shocking defeat. Here are the worst losses of Iron Mike Tyson’s iconic career. 

Buster Douglas

Later this year, a 57-year-old version of the former heavyweight icon will face off against YouTuber-turned-boxer Jake Paul in a moneyspinning clash hosted live on Netflix. The latest Jake Paul vs Mike Tyson betting odds makes the former a 2/5 favorite for victory, primarily thanks to him being in his athletic prime and his opponent being closer to retirement age than in his glory days. However, even if he does go on to get the victory, it won’t be the most shocking upset in boxing history. 


The latest boxing odds currently have Tyson priced as a 13/5 outsider for the upcoming bout. That is nothing close to the 42/1 odds that rank outsider James ‘Buster’ Douglas had when he faced off with iron Mike back in February 1990 in Tokyo, Japan for the undisputed heavyweight championship of the world. The reigning champion was seemingly invincible at the time, 37-0 with 34 knockouts. 

However, from the opening bell, it was clear that the underdog was not intimidated by the champ’s fearsome reputation. He utilized his reach advantage and jab to keep the champion at bay, while also displaying surprising aggression and confidence. As the rounds progressed, Douglas continued to dominate, landing powerful combinations that left the huge favorite visibly frustrated and out of sorts.

In the tenth round, Douglas delivered a stunning uppercut followed by a flurry of punches that sent Tyson sprawling to the canvas. The sight of him fumbling for his mouthpiece, dazed and unable to beat the count, remains one of the most iconic images in boxing. Douglas’ victory not only ended Tyson’s unbeaten streak but also shattered the aura of invincibility that had surrounded him up until that point. 

Evander Holyfield

Evander Holyfield and Mike Tyson’s rivalry is one of the most storied in boxing history, marked by two memorable bouts. Their first encounter in November 1996, saw Holyfield, a former heavyweight champion, come out of retirement to face the Baddest Man on the Planet. He was four fights into his comeback and at the age of 34, the likes of controversial promoter Don King believed that he was finished. Many expected the WBA Champion to steamroll him and retain his belt, but instead, it was he who emerged victorious, winning by an 11th-round TKO.

The rematch seven months later, however, would become infamous for an entirely different reason. From the outset, Holyfield’s “accidental” head-butting tactics seemed to unsettle his opponent, who became increasingly frustrated as the bout progressed. 

In the third round, that frustration boiled over. 

In one of the most bizarre moments ever caught on camera, Tyson visibly tore off a chunk of Holyfied’s ear with a bite before spitting it onto the canvas. The fight was temporarily halted, and when it resumed, he went for his other ear just seconds after the restart. This act of desperation led to a disqualification defeat and a $3 million fine, forever tainting his legacy. 

Christopher Stern

Christopher Stern is a Washington-based reporter. Chris spent many years covering tech policy as a business reporter for renowned publications. He has extensive experience covering Congress, the Federal Communications Commission, and the Federal Trade Commissions. He is a graduate of Middlebury College. Email:[email protected]

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