The biggest upsets in boxing history

Mike Tyson vs Buster Douglas

James ‘Buster’ Douglas was a 42-1 underdog going into his undisputed world heavyweight title challenge to 37-0 Mike Tyson, who was defending his world titles for a 10th time.

Unbeaten with an 89% KO ratio, ‘Iron Mike’ had blasted 17 of his opponents away in just one round up to this point in February 1990, before meeting Buster Douglas in Tokyo, Japan.

From Ohio, Douglas was 29-4-1 and had already lost his prior world title challenge to Tony Tucker in 1987, who Tyson had defeated just two months later.

Douglas surprisingly dominated Tyson, landing big hooks in close and matching the formidable champion’s aggression, yet he was dropped heavily in the eighth by a signature Tyson uppercut, but he returned to his feet to continue the fight. 

Then, in round 10, Douglas launched a ceaseless attack that ended with Tyson on the deck, unable to get back up again. Ironically, the match was titled, ‘Tyson is Back!’, but ended with Tyson on his back!

Before the fight, commentators said on air that they were expecting another 90-second annihilation.

Tyson’s personal life issues, such as his rocky relationship with Robin Givens, contract disputes with managers and promoters, his departure from longtime trainer Kevin Rooney, and an entourage that was draining all his funds, all contributed to his first career defeat.

Sugar Ray Robinson vs Randy Turpin

Yet another incredible upset involving a British fighter, which some would argue comes above Honeyghan’s win over Curry due to Sugar Ray being widely regarded as the greatest fighter of all-time.

Before the days of governing bodies, Sugar Ray Robinson was the undisputed middleweight champion with the NBA, NYSAC and The Ring titles. His fight with Turpin was the last leg of his European tour and had lost just once in 132 bouts at this point, which was to Jake LaMotta, which he avenged five times.

Turpin took the fight to Robinson, who struggled with his awkward style and physical strength. When his hand was raised after 15 rounds, Turpin became the first British boxer to win a world middleweight title in 60 years since Bob Fitzsimmons in 1891.

Don Curry vs Lloyd Honeyghan

Lloyd Honeyghan’s victory over Don Curry is the single biggest upset involving a British boxer in the history of the sport.

‘Honey’ was a respectable 27-0 going into the undisputed welterweight championship contest in Atlantic City, but the American had made seven title defences and widely considered to be the pound-for-pound No.1.

The Jamaican-born, British boxer was dismissed by the American champion as any kind of threat, even asking, “Who is this ragamuffin man?”, which the Bermondsey boxer proudly adopted as his nickname thereafter.

The underdog dominated Curry to break his nose, split his lip and cut his eye, which required 20 stitches later.

Honeyghan’s confidence was reflected in his $5,000 bet on himself at the bookies, earning an additional $30,000.

Evander Holyfield vs Mike Tyson

Mike Tyson vs Evander Holyfield in 1996 was billed as ‘Finally’, as the intended matchup was delayed several times, initially agreed in 1990 but the loss to Buster Douglas, derailed that. “The Real Deal” got a shot at the new champion instead and won via third-round knockout. A date was given for November 18, 1991, but Tyson was held up by a rematch with Donovan Ruddock, after their first fight ended in controversy; then an injury, and then imprisonment!

Holyfield became the cruiserweight division’s first-ever undisputed champion, then he conquered he world again at heavyweight. But despite this success, he entered the championship clash with Tyson as a 5/1 underdog.

Tyson came out of the corner fast, as is customary with the aggressive swarmer, and sent Holyfield reeling backwards with his first solid punch. But Holyfield had studied Tyson extensively and hired David Tua as his sparring partner to replicate his style, but was surprised to find that he was the stronger of the two when they leaned into and pushed each other.

After a few rounds, Tyson was being comprehensively outboxed and was dropped in the sixth round. By round 10, he was out on his feet, but was sent back out by his corner for the 11th round. After another one-sided beating, the referee had seen enough and stopped the contest in the penultimate round, giving Holyfield one of the most famous upset victories in the history of boxing.