The 15 biggest upsets in boxing history

15 of the biggest upsets in boxing history

Boxing is a sport that creates more drama and euphoria than any other sport, and the biggest upsets send shockwaves around the world to get everyone talking; not just for the many days afterwards, but years and years later.

When thinking of the biggest upsets in boxing history, there’s one fight that comes to mind above all others, even though it took place four decades ago.

Read on to discover SportsBoom’s top 15 biggest upsets in boxing.

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.

Lennox Lewis vs Hasim Rahman

Another undisputed champion took an unexpected fall from grace, but over a decade later than Tyson’s biggest upset.

In April 2001, Lennox Lewis defended his WBC, IBF, IBO and Lineal championships to huge underdog Hasim Rahman in South Africa.

With sights set on a superfight with Mike Tyson, who was issued a suspension for testing positive for marijuana, British boxing legend Lewis instead opted to defend against IBF #2 Rahman, who was a 20-1 underdog.

However, the Baltimore boxer arrived a month prior to the bout to acclimatise to Guateng, which is 5,200 feet above sea level. The champion mistakenly didn’t turn up until 12 days before.

Lewis ‘The Lion’ was ahead after the first four rounds, but he was far too comfortable and complacent. Despite being stalked around the ring, Rahman pushed Lewis back with a series of jabs, only for Lewis to smile at him with his hands held down low, so ‘The Rock’ threw a huge right hand to KO the king in the fifth round.

Lewis avenged the defeat in November that same year, and even went one better with a fourth-round knockout.

Muhammad Ali vs Sonny Liston

Sonny Liston throws a punch against Muhammad Ali//Getty Images

Then known as Cassius Clay, in February 1964, Ali was an 8-1 underdog going into his first world title fight with the fearsome champion, Sonny Liston, who had defeated eight of the top 10 contenders at heavyweight, seven by knockout.

Liston was known as the biggest puncher ever in the sport and was widely considered as unbeatable after two back-to-back first-round KOs over Floyd Patterson. 

No one expected ‘The Louisville Lip’, who had been knocked down twice in his career already, to win and no one particularly wanted him to either, as his braggadocio, and disrespectful comments and behaviour towards his opponents earned him a considerable dislike among reporters and fight fans.

In fact, he was so disliked by the press that 43 from 46 writers had picked Liston to win by knockout.

However, it was Clay who shocked the world when he forced “the big, ugly bear” to retire on his stool after six one-sided rounds. At 22, Clay became the undisputed champ and youngest boxer ever to dethrone a reigning heavyweight world champion.

15 months later, Ali stopped Liston even earlier with a first-round KO, which some believe was a fight that Sonny threw after ‘The Phantom Punch’ landed.

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, earning an additional $30,000.

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.