Top 20 Biggest Upsets in Boxing History

Top 20 Biggest Upsets in Boxing History

Each boxing match contains that trademark unpredictability, but some bouts take it and turn it into a shock. The greatest shocks in boxing are where the game’s living soul lies.

when the perceived lesser light fights back, the king is dethroned, and the world is left shocked. No, these are not simply shocks; they alter careers; rewrite history, and put across the profound truism of the squared circle – all bets are off.

Disappearing blows, verbal altercations, rage-induced punches, and more, it’s time to look into the showdown of boxing’s top 20 most shocking upsets ever.

 

What is an Upset in Boxing?

In boxing, an upset is a situation in which a loser or inferior fighter, one who is expected to lose the fight because of lower ranking, lack of experience, or perceived ability, beats his superior or more favoured opponent. 

It has repercussions for both fighters and their supporters of what an upset could mean. For underdogs, it can enhance their career, image, and, occasionally, their standing and bring them better opportunities for more attractive fights.

When the favourite loses such a match, it becomes a tragedy but it is the usual time that the boxer has to evaluate the strategies he or she applied, the training regimen adopted, or even the career. To fans and even other analysts, upset can be entertaining because it surprises people and sometimes brings drastic changes in the sporting arena.

 

Top 20 Biggest Upsets in Boxing Right History

Below are the biggest upsets in boxing history:

 

  1. Carlos Baldomir vs. Zab Judah

Baldomir was seen as a stepping stone for Judah, who expected an easy win to secure a title shot against Floyd Mayweather. This confidence likely led Judah to underestimate him.

However, Baldomir had a plan of his own, keeping his focus despite Judah’s antics—like a low blow during introductions. Baldomir dominated most of the fight, earning a unanimous decision. He later faced Mayweather, where he suffered his first professional loss.

 

  1. Iran Barkley vs. Thomas Hearns

Barkley was a heavy underdog for good reasons. Hearns had been a force in the middleweight division, with his only losses against top-tier fighters like Sugar Ray Leonard and Marvin Hagler.

As expected, Barkley lost the first two rounds but turned the tide in the third, dropping Hearns and forcing a stoppage before Hearns could recover.

 

  1. George Foreman vs. Joe Frazier

Foreman already had a reputation as a powerful puncher but was still considered unrefined. Frazier, with wins over big names like Muhammad Ali, was seen as a tough challenge.

On paper, Frazier’s style seemed suited to handling Foreman. But Foreman’s strength proved overwhelming, as he knocked Frazier down three times in the first round and three more in the second, forcing the referee to stop the fight.

 

  1. Michael Spinks vs. Larry Holmes

Holmes, the IBF heavyweight champion, was undefeated in 48 fights when he faced Spinks, the reigning light-heavyweight champion moving up in weight. Many doubted Spinks could be a real threat due to his smaller size.

However, Spinks used his speed to outbox Holmes over 15 rounds, ultimately earning a controversial decision.

 

  1. George Foreman vs. Michael Moorer

At 45, Foreman challenged Moorer for the WBA and IBF titles. Moorer had recently captured both belts by defeating Holyfield and wanted a high-profile opponent to reinforce his reign as champion.

Many fans saw this as a mismatch, with Foreman thought to be past his best years. Yet, Foreman shocked everyone by knocking out Moorer in the tenth round, becoming the oldest heavyweight champion in history.

 

  1. Antonio Tarver vs. Roy Jones Jr.

In their first encounter, Tarver lost a close decision, though many fans believed he deserved the win. Tarver felt he’d been unfairly denied, while Jones was frustrated that fans questioned his victory.

In their rematch, Tarver pulled off one of boxing’s biggest upsets, knocking out Jones in the second round—the first time Jones had ever been stopped.

 

  1. Lloyd Honeyghan vs. Donald Curry

Curry, with a 25-0 record and multiple titles, was seen as the best welterweight since Sugar Ray Leonard. Few knew much about Honeyghan, despite his solid 27-0 record, and U.K. fighters were often viewed as less competitive than their U.S. counterparts.

However, Honeyghan dominated Curry, forcing him to quit after the sixth round to avoid further punishment.

 

  1. Hasim Rahman vs. Lennox Lewis

Lewis, having become an undisputed heavyweight champion by beating Holyfield, appeared unstoppable. Yet Rahman considered a massive underdog with only a single notable win, delivered a stunning upset.

Near the end of a round, he landed a huge shot that floored Lewis, ending his reign. Rahman’s victory was short-lived, as Lewis avenged the loss with a fourth-round knockout in their rematch.

 

  1. Kirkland Laing vs. Roberto Duran

Duran had faced some tough losses leading up to his fight with Laing, including defeats by Leonard and Wilfred Benitez. Still a formidable opponent, Duran had solidified his place as one of the sport’s all-time greats.

Despite being unknown, Laing outclassed Duran, securing one of boxing’s biggest upsets—a loss that eventually set the stage for Duran’s inspiring comeback.

 

  1. Sugar Ray Leonard vs. Marvelous Marvin Hagler

Hagler, widely seen as the top middleweight and among the best pound-for-pound fighters, hadn’t come close to losing in over a decade. Although Leonard was smaller, he used his speed and technical skills to edge out a narrow, controversial decision, pulling off a memorable upset. 

 

  1. Tyson Fury vs. Wladimir Klitschko  

In one of the most stunning upsets in boxing history, Tyson Fury, known as the “Gypsy King,” entered the fight as the underdog but delivered a masterclass in Germany against unified champion Wladimir Klitschko.

Despite criticisms over his brash personality and unconventional physique, Fury outmaneuvered Klitschko with his reach, speed, and skill, completely neutralizing the Ukrainian’s offense and securing a unanimous decision victory. 

At the final bell, Fury famously sang to the crowd, marking his historic achievement. Although a rematch was anticipated, mental health challenges and other setbacks kept Fury out of the ring for a time. He later returned triumphantly, claiming victories on big stages, including Las Vegas and Wembley.

 

  1. Randy Turpin vs. Sugar Ray Robinson  

This 1951 fight in London broke the mold outside the heavyweight division. British underdog Randy Turpin, against all odds, halted Sugar Ray Robinson’s incredible 90-fight winning streak to secure a monumental victory.

Turpin capitalized on Robinson’s fatigue to win a thrilling contest, only to lose in the rematch two months later. Robinson rebounded decisively, securing a career-defining victory and adding to his legendary 132-fight career.

 

  1. Muhammad Ali (Cassius Clay) vs. Sonny Liston  

In this breakout fight, a young Muhammad Ali—then known as Cassius Clay—defied expectations to dethrone the formidable Sonny Liston, a dominant force in the division.

Ali’s stunning performance, causing Liston to retire on his stool after six rounds, showcased his talent and confidence, which would later make him an iconic figure both in and out of the ring.

 

  1. Frankie Randall vs. Julio Cesar Chavez  

Julio Cesar Chavez, with an astounding 90-fight win streak, seemed untouchable before his 1994 bout with Frankie Randall in Las Vegas. Despite being heavily favored, Chavez was outboxed by Randall, who won a hard-fought contest after two-point deductions against Chavez.

The fight concluded in an upset victory for Randall, sparking jubilant celebrations, although Chavez would avenge his loss just a few months later.

 

  1. Muhammad Ali vs. George Foreman  

The “Rumble in the Jungle” ranks among the greatest upsets. George Foreman was the reigning champion and was widely expected to defeat Ali, who was regarded as past his prime.

Employing the clever “rope-a-dope” strategy, Ali absorbed Foreman’s blows, eventually knocking him out in the eighth round, securing his legacy with one of the most celebrated wins in boxing history.

 

  1. Evander Holyfield vs. Mike Tyson  

The rivalry between Evander Holyfield and Mike Tyson is unforgettable, with their first fight being a massive upset. Holyfield entered the ring as a 25/1 underdog against the feared Tyson, who had been on a streak of knockouts following his release from prison.

Holyfield managed to frustrate Tyson throughout, ultimately finishing the fight in the 11th round. Their rematch, infamous for Tyson’s ear-biting disqualification, is etched in boxing lore, though the two have since reconciled.

 

  1. Corrie Sanders vs. Wladimir Klitschko  

Corrie Sanders shocked the world in a 2003 bout, going up against the heavily favored Wladimir Klitschko. Sanders, who had barely fought in two years, stunned Klitschko with powerful punches in the first round and continued the assault in the second, eventually winning by stoppage.

His victory was a national celebration in South Africa, though his title reign was brief, as Klitschko’s brother Vitali reclaimed the belt soon after.

 

  1. Andy Ruiz Jr vs. Anthony Joshua  

Anthony Joshua, the undefeated unified champion, faced late replacement Andy Ruiz Jr. in a 2019 fight. Despite Ruiz being a significant underdog, he recovered from an early knockdown to shock the boxing world, stopping Joshua after multiple knockdowns.

Ruiz’s unlikely victory echoed a real-life “Rocky” story, although Joshua regained his belts in a rematch.

 

  1. Leon Spinks vs. Muhammad Ali  

In one of the greatest upsets of the time, Leon Spinks, with just seven professional fights, defeated Muhammad Ali, who boasted a stellar 55-2 record. Spinks earned a split-decision win in a dramatic 15-round fight.

Ali later won a rematch, marking the end of his legendary career, as he suffered further losses before retiring.

 

  1. Buster Douglas vs. Mike Tyson  

The biggest upset on this list, Buster Douglas’s victory over Mike Tyson in 1990, remains legendary. Tyson entered the bout with a perfect 37-0 record and was considered unbeatable.

Despite suffering a knockdown, Douglas rose to his feet and, in the tenth round, shocked the world by knocking out Tyson. Although Tyson’s career continued strong, this loss marked a major turning point in boxing history.

 

Frequently Asked Questions (FAQs)

Who is the one with the most knockouts in boxing?

With 138 knockouts to his credit, Billy Bird is highly placed among the most successful knockout punchers in boxing history. That is a record and it affirms the dynamism and force he used in the sport between times and classes.

What is the glove used to mark the defeat of a fighter in the ring called?

A fighter drops his/her towel on the row, instructing the referee to halt the boxing bout.

What was the original name given to Muhammad Ali?

Surprisingly, before he converted into a Muslim and before he had the privilege to later be known as the Great Muhammad Ali, Clay had a quite long name for a baby – his actual name was Cassius Marcellus Clay Jr.

In professional boxing, how many pounds does the cruiserweight division extend up to?

The permitted weight for a cruiserweight is 200 pounds.

Who has knocked down most world champions?

Currently, Floyd Mayweather stands as a man who has credited titleholders and world champions with 23 wins in boxing without having a title himself. This is slightly above 44% of his fights, and the opponents he fought are considered some of the best in the business.

 

Conclusion

In boxing where there are planned strategies, hard work, training and so on defining each fight the biggest upsets bring back the essence of the game. Such triumphs have turned over narratives and brought down colossuses wherein the boxing ring makes no pretense of a lemonade stand.

They are living testaments that nobody can and will succeed against faith, determination, heart and so much more than an underdog spirit. 

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