5 Biggest Upsets in Boxing History

Many boxing fans faithfully watch the sport because it’s an adrenaline-pumping and action-packed extravaganza. Boxing has a rich history of unforgettable matchups that have entertained people for centuries. But no matter who a fan is rooting for, everyone will agree that there’s nothing quite as thrilling as watching an unexpected knockout from an underdog. Remember David and Goliath? This story is not just for books because these encounters have happened in the boxing arena, wherein an unassuming little guy defies all odds and takes down a champion. 

Many memorable moments in the ring have left fans impressed, amazed, and shocked to the core. These dramatic boxing upsets are a testament to the sport’s unpredictable nature. In fact, this would be a good sociological research topic or even a high school essay. Students will feel inspired to do the work and not ask anyone to write my essay for me because boxing upsets are a great source of inspiration and motivation for anyone who has ever been in the position of the underdog. 

Even non-boxing fans will find such thrilling matches the perfect introduction to the ring’s excitement and drama. As an audience, it’s good to remember that anything can happen in an arena when the bell rings. Even a small fry might come out on top and beat an undefeated champion. Let’s dive deep and take a closer look at the biggest and most unforgettable upsets in boxing history that have left audiences stunned. 

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Manny Pacquiao versus Juan Manuel Marquez IV in 2012

Manny Pacquiao, aka the PacMan, is a boxing legend with many world titles in various weight classes. Proof of his accomplishments? He has battled stars like Oscar De La Hoya, Floyd Mayweather Jr., and Miguel Cotto. But what unforgettable upset to his stellar track record occurred in 2012 when he had a match-up with Juan Manuel Marquez. Prior to that, they had fought three times wherein Marquez succumbed to Manny’s: 

  • Forceful fist
  • Powerful punches
  • Incredible speed
  • Agility in the ring
  • Adaptability in fighting various opponents

But in this particular meeting at the MGM Grand in Las Vegas, Pacquiao suffered a devastating loss. Marquez shocked the world by knocking out PacMan with a few seconds remaining in the sixth round. This memorable encounter ended Pacquiao’s 7-year winning streak while establishing Marquen as a formidable fighter. At the same time, this also sparked a debate among the fans as Marquez was rumored to have used performance-enhancing drugs. 

Buster Douglas versus Mike Tyson in 1990

Iron Mike is a name that strikes fear and makes knees shake in the world of boxing. This moniker belongs to none other than the legendary fighter Mike Tyson. Iron because of his iron fist, powerful punches, and iron-clad body that could endure massive hits. For three years (1987 to 1990), he was the undisputed heavyweight champion with an astonishing record of 37-0. Amazingly, 33 of those wins were knockouts. He was so good at his craft that a Nintendo game was fashioned after him. 

However, in February 1990, Buster Douglas shocked the world by defeating Tyson in the 10th round. Despite his fatigue and banged-up body, Douglas unleashed a bevy of dynamic punches, including a powerful uppercut, that sent Iron Mike to his knees. He could not return to his feet before the 10-count, ending the fight in Douglas’ favor. It was a shocking defeat but a sweet victory for Douglas, written off by critics as a sure loser before the fight.

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Buster Douglas versus Evander Holyfield in 1990

James “Buster” Douglas was on a roll at the start of this new decade. After his stunning defeat of Iron Mike, he was tasked to battle Evander Holyfield. The latter was another professional fighting legend. He won the heavyweight championship a whopping four separate times. He had surpassed Muhammad Ali, who won it thrice. 

In this face-off, Buster was considered once again the underdog. Fortunately, he exhibited the same power, agility, and endurance that put Tyson down. He proved his mettle by winning in a split decision after 12 boxing rounds. The dramatic win is another upset as people forecasted that Holyfield, the more professional fighter, would prevail. This win proved that Buster’s win against Tyson was not luck. He is a fighter to be reckoned with and not just a one-hit-wonder. 

Muahmmad Ali versus Sonny Liston in 1964

For a long time, Muhammad Ali has been synonymous with boxing success. Many fans are familiar with this amazing fighter, even in this new century. Many people see the accolades and forget the struggle along the way. Remember, like any neophyte, Ali had to serve his dues, training relentlessly and working hard to create a name for himself amidst boxing giants. 

Fortunately, his lucky break came in the early 60s in an exciting Miami Beach match. He was tasked to face off with Sonny Liston, a beloved American pro boxer, for the heavyweight title. At that time, Liston was an intermediate fighter, the crowd favorite expected to win over Ali, who was just a budding 22 years old. 

It was an exciting fight as Liston was gungho to get the heavyweight title. But Ali’s speed and agility tested his endurance. Finally, in the 7th round, Liston threw in the towel and admitted defeat. Ali won the match and the coveted title. This dramatic encounter marked the beginning of Ali’s legendary ascent as an indefatigable champion. Who would have thought that a simple fight would be a defining moment for his career? 

Leo Spinks versus Muhammad Ali in 1978

By the 70s, Ali had established himself as one of the greatest fighters. When he met Leo Spinks, the odds were in his favor. Leo was a newbie with only seven professional fights on his roster back then. What everyone thought was a match in the bag proved to be a major disappointment. Much to the fan’s chagrin, Spinks defeated Ali in a split decision and became the new heavyweight champion at 24 years old. 

Final Thoughts

These boxing upsets are just a few examples. But there’s nothing like an unexpected knockout punch or swift decision in favor of an underdog to create an uproar in the boxing arena. Although this may be unsettling for fans, these encounters eventually become cemented in boxing history and move on to become legacy. 


Integral part of the Irish boxing community for over 13 years