The 20 Biggest Upsets In Boxing History

There’s a tiny part of us that always roots for the underdog in boxing. No one gives them much of a chance to emerge victorious, but they find a way to do so based on sheer will and determination. It’s one of the reasons why combat sports are so popular. Nothing beats an underdog surmounting impossible odds to make their dreams a reality.

This article will explore some of the most memorable upsets in boxing history and relive the stories behind them. 


The 20 Most Memorable Upsets In Boxing History

Ready to find out who pulled off the biggest upsets in boxing history? Let’s jump right into our list:


1) Buster Douglas Vs Mike Tyson

Buster Douglas is the standard all upsets in combat sports are now measured with. No one gave him much of a chance heading into his title bout against Tyson. At the time, Tyson sported a 37-0 professional record, with most of his wins coming via vicious knockouts. 

Douglas was a mediocre boxer who had blown his first chance to secure a championship when he faced Tony Tucker for the IBF heavyweight title. The oddsmakers gave him a 42:1 underdog, which seemed about right heading into the fight. 

Douglas surprisingly held his own as the fight progressed, and he survived the count when Tyson dropped him in the eighth round. Douglas went on to knock Tyson out in the tenth round, securing the biggest upset in combat sports history. If you had bet S$100 on Douglas, you’d have walked away with S$4,200. 


2) Leon Spinks Vs Muhammad Ali

Ali was nearing the end of his legendary career when he squared off against Spinks in 1978. Spinks only had seven professional fights under his belt at the time, and few believed that would be enough to get past albeit an aging Ali. 

Spinks went on to put on the best performance of his boxing career during his 15-round action-packed fight, edging out the decision. Unfortunately for Spinks, he lost the rematch several months later and never lived up to the high expectations many placed on him. 


3) Randy Turpin Vs Sugar Ray Robinson

Robinson was on a 90-fight winning streak when he defended his NYSAC, NBA, and The Ring middleweight titles against Turpin. Turpin was a 20:1 underdog, and many expected the Brit to be in over his head when he stepped inside the ring against Robinson. 

However, Turpin proved to be a better fighter than many people gave him credit for, and he took full advantage as Robinson’s gas tank ran on fumes later in the fight. That earned him a decision against one of the greatest boxers ever. Robinson got his revenge and knocked Turpin out when the two fought again a few months later.  


4) Muhammad Ali Vs Sonny Liston

This was one of the fights that paved the way for Ali’s greatness. Liston was one of the scariest fighters of his era, and he was coming off consecutive wins against Floyd Patterson, who was the man before Liston beat him. 

Many people expected things to go bad for the big-talking Ali when he stepped inside the ring to face Liston. Ali shocked the world by outclassing Liston so severely that he quit on his stool after only six rounds. It was then the boxing world realized Ali could back up most of the checks his mouth wrote. 


5) James Braddock Vs Max Baer

This upset was so colossal Braddock became known as “The Cinderella Man,” and his story became an award-winning movie. Max Baer was a powerful puncher with a reputation for knocking opponents out and was the newly minted Ring, NBA, and NYSAC heavyweight champion.

Braddock was meant to be an easy payday for Baer despite a few recent respectable wins under his belt. The oddsmakers had Braddock as a 10:1 underdog heading into the fight. He surprised fans with his ability to take a shot, took everything Baer had, and kept walking forward. 

That earned him a unanimous decision and three heavyweight titles. Unfortunately for Braddock, his title reign was short-lived as he lost his next fight to Joe Louis. 


6) Max Schmeling Vs Joe Louis

Louis had already established himself as a force to be reckoned with in the heavyweight division when he squared off against Schmeling. Sporting a 24-0 professional record, few expected Schmeling to put up much of a fight against the hard-hitting Louis. 

However, Schmeling had appropriately prepared for the fight and studied Louis’ tendencies. His hard counter rights kept finding their target. He eventually put Louis away with his barrages during the twelve round, handing the Brown Bomber his first loss. Louis went on to knock Schmeling out during their rematch. 


7) Lloyd Honeyghan Vs Donald Curry

Many considered Curry to be the best thing in the welterweight division since Sugar Ray Leonard. He had secured multiple titles at that point in his career and sported a 25-0 professional record. Fans barely knew who Lloyd was heading into the fight, even though the Brit sported a respectable 27-0 record. The competition in the U.K. wasn’t seen as comparable to the competition in the U.S., so many expected Curry to outclass him. 

That’s not what happened inside the ring, though. Lloyd was so dominant during the fight that Curry quit in his corner after the sixth round to stop the humiliating beating he was receiving. 


8) Evander Holyfield Vs Mike Tyson

Tyson lost a lot of his mystique as a boxer after his loss to Buster Douglas, but he managed to restore his reputation after a stint in prison. He went back to steamrolling opponents as he did during his earlier days, looking as ferocious as he ever did inside the ring. 

Holyfield was considered a washed-up boxer then, and he opened up as a 25:1 underdog. However, Holyfield lived up to his nickname “The Real Deal” and showed the boxing world he was indeed the real deal. Holyfield frustrated Tyson by outboxing him and clinching up whenever Tyson let his hands go. He knocked him out in the 11th round and proved his victory wasn’t a fluke by dominating their rematch before Tyson was disqualified for biting his ear. 


9) Muhammad Ali Vs George Foreman

This was one of the biggest fights that ever took place in boxing history, and it lived up to the hype. Foreman, the reigning WBC, WBA, and Ring heavyweight champion, was the “Mike Tyson” of his day, and no one had been able to figure out how to beat him. 

Ali was also established at that point, but Joe Louis and Ken Norton had beaten him. Many didn’t give Ali much of a chance, but that didn’t stop him from throwing every insult he could at Foreman. Ali backed his talk up inside the ring, using the rope-a-dope strategy to tire Foreman before knocking him out in the eighth round.  


10) Fritzie Zivic Vs Henry Armstrong

Known as Homicide Hank during his prime, Armstrong successfully defended the world welterweight title eighteen times, and it was a foregone conclusion that Zivic would be number nineteen. Zivic shocked fans when he proved too much for Armstrong, coming close to finishing him during the final round. Zivic earned a decision victory and one of the biggest upsets in boxing history. 


11) Sugar Ray Leonard Vs Marvelous Marvin Hagler

Marvelous Marvin Hagler was widely regarded as the best middleweight of his era and one of the pound-for-pound best in the world when he fought Leonard. No one had come close to beating Hagler in over a decade, and Leonard was the smaller fighter. 

However, Leonard used his speed and technical prowess to edge out a close decision, scoring a controversial upset. 


12) Kirkland Laing Vs Roberto Duran

Duran had already suffered a few humiliating defeats by the time he faced Laing. He gave up against Leonard and was badly beaten by Wilfred Benitez. However, Duran was still dangerous inside the ring and had earned his status as one of the all-time greats. 

At the time, Laing was an unknown boxer, but that didn’t stop him from outclassing Duran and scoring one of the biggest upsets in boxing history. The loss turned out to be a good thing for Duran as it set up one of the most inspiring comeback stories in boxing. 


13) Hasim Rahman Vs Lennox Lewis

Lewis was the heavy favorite heading into his fight against Rahman, and for good reason. He was the undisputed heavyweight champion, an honor he won by defeating Evander Holyfield. 

On the other hand, Rahman’s career appeared to be going the wrong way. He didn’t have a bunch of notable wins on his resume, with his only impressive victory coming against Corrie Sanders. Lewis was expected to walk through him, but Rahman was the one who scored a knockout in the fifth round. 


14) Frankie Randall Vs Julio Cesar Chavez

Chavez started his boxing career with 90 consecutive fights without a loss, with a draw against Pernell Whitaker. No one expected Chavez to struggle against Randall. Both men put on an impressive show during their 12-round showdown, with Randall sending Chavez to the canvas for the first time in his career during the 11th round. Randall won a split decision, scoring the upset victory against a legend of the sport. 


15) Antonio Tarver Vs Roy Jones Jr.

Tarver lost a close decision the first time these two shared a ring, but many fans felt he won the fight. Tarver claimed the judges robbed him, and Roy was insulted by the fact many fans didn’t think he won fair and square, setting the stage for the rematch. 

Tarver then pulled off one of the biggest upsets in boxing history, knocking Jones out during the second round of their showdown. It was the first time Jones Jr. was stopped during his career. 


16) George Foreman Vs Michael Moorer

Foreman was 45 years old when he challenged Moorer for the WBA and IBF titles. Moorer had just won the belts by defeating Holyfield, and he was looking for a big name to solidify his status as the heavyweight champion. 

Many fans viewed the matchup as lopsided as Foreman was past his prime, but he proved them all wrong when he knocked Moorer out during the tenth round, becoming the oldest heavyweight champion in boxing history. 


17) Michael Spinks Vs Larry Holmes

Holmes was the IBF heavyweight champion when he shared a ring with Spinks. He was also on a 48-fight winning streak. Spinks was the reining light-heavyweight champion who moved up a weight class to challenge Holmes, and many felt he was too small to be a legitimate threat. 

Spinks used his speed advantage to outbox Holmes for 15 rounds, earning himself a controversial decision. 


18) George Foreman Vs Joe Frazier

Foreman had already developed a reputation as a powerful puncher before his fight against Frazier, but his skills were still raw for the most part. Frazier was the man in the division with wins over big names like Muhammad Ali. 

On paper, Foreman looked like the perfect opponent for Frazier’s style, but Foreman used his size and strength to wear Frazier down, sending him to the canvas three times in the first round and another three times in the second round before the referee stopped the fight. 


19) Iran Barkley Vs Thomas Hearns

Barkley wasn’t given much of a chance against Hearns for many good reasons. Hearns was one of the most dominant forces in the middleweight division, and his only losses were against exceptional boxers like Sugar Ray Leonard and Marvin Hagler. 

As most people expected, Barkley lost the first two rounds, but he turned things around when he dropped Hearns in the third round. Hearns got back to his feet, but Barkley never gave him a chance to recover, forcing the stoppage during the same round. 


20) Carlos Baldomir Vs Zab Judah

Baldomir was supposed to be a journeyman Judah would beat up to earn a title shot against Floyd Mayweather, and that probably made him overconfident heading into the fight. Carlos had plans of his own, and he didn’t let Judah’s antics, like throwing a low blow during introductions, get into his head. He outclassed Judah for most of the fight, winning a unanimous decision. Baldomir went on to face Mayweather and suffered his first professional loss. 


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