The 5 Most Shocking Upsets In Boxing History

In the sport of boxing, there is always a favorite and an underdog heading into any given fight. Whether determined through betting odds, or through a simple analysis of a bout’s complexion, fans get a general idea of who is supposed to win on fight night.

The favorite, of course, is expected to earn the win one way or another. He owns a perceivable advantage and has a clear path to success. However, when things don’t exactly go the favorite’s way is when it gets interesting. It then becomes the underdog’s job to derail the favorite and claim victory for himself.

When an underdog is able to emerge victorious, it’s called an upset. Boxing is abundant with stories of epic upsets embedded deep in its rich history — tales of fighters who were all but written off, only to end up capturing elusive glory.

Boxing is often called the ‘theatre of the unexpected’, due to its unpredictable nature. You may think you know what will happen in a bout, but the sport will almost always surprise you.

Everyone loves an underdog story, and here we take a closer look at a handful of successful underdogs who were able to turn the tables and win. Today, Evolve Daily shares the five most shocking upsets in boxing history.

5) Tyson Fury Upsets Wladimir Klitschko

November 28, 2015

ESPRIT Arena, Dusseldorf

Unbeaten English heavyweight Tyson Fury is brash and outspoken and has a cult following chanting his name every time he steps into the ring. Against the great Wladimir Klitschko in 2015, Fury’s rabid fans traveled to Dusseldorf to chant his name, as the British boxer scored the biggest win of his career — a stunning upset of one of the most dominant heavyweight champions in recent times.

Fury earned a unanimous decision on all three judges’ scorecards, tallying 115-112, 115-112, and 116-111 in an exciting contest that saw Fury become the unified heavyweight world champion. After having started extremely fast and taking Klitschko out of his comfort zone, Fury picked his opponent apart from the outside, using his length and reach.

It was a high-level chess match in the ring and one that Fury would emerge from as an unlikely winner. To be fair, Father Time had caught up with Klitschko, and he just looked old and slow for the majority of the bout.


4) Antonio Tarver Stops Roy Jones Jr.

May 15, 2004

Mandalay Bay Resort & Casino, Las Vegas, NV, USA

After losing a razor-thin majority decision to Roy Jones Jr. in their first encounter, Antonio Tarver faced Jones once again in an immediate rematch six months later. This time, the “Magic Man” was able to finally defeat Jones, becoming the unified light heavyweight champion of the world.

The fact that Tarver beat Jones wasn’t the most shocking part of it all, however, it’s how he did it. Up until that bout, Jones was the top pound-for-pound fighter in boxing. The way he decimated his opponents with a unique flair and championship swagger, it was truly extraordinary.

When Tarver finally dealt Jones the most devastating loss of his career — a shock second-round technical knockout — he was never the same boxer again. The two would rematch again in 2005, but Tarver won that bout too, proving he truly had Roy’s number.


3) Manny Pacquiao Retires Oscar De La Hoya

December 6, 2008

MGM Grand, Las Vegas, NV, USA

Filipino ring icon and multi-division boxing world champion Manny “Pacman” Pacquiao is a true legend of the sport, winning titles across eight different weight classes throughout his career. He made his name as a Pacific storm in the early 2000’s, defeating some of the biggest names from flyweight to lightweight en route to becoming a pound-for-pound entrant.

When longtime boxing analyst Larry Merchant first introduced the idea of Pacquiao climbing up in weight to face Oscar De La Hoya, however, everyone thought he was crazy. But just months after the match was suggested, it became a reality.

Pacquiao met De La Hoya, then a natural middleweight, in one of the most memorable bouts in history. De La Hoya cut weight to face the Filipino superstar, and Pacquiao jumped up two divisions to meet him at welterweight. It was billed as “The Dream Match”.

Needless to say, Pacquiao was the much smaller man by a large margin and headed into the bout a huge underdog. No one could fathom how a former flyweight would be able to beat a middleweight legend.

In the fight, however, Pacquiao gave De La Hoya the worst beating of his career, using his speed and power to completely destroy “The Golden Boy” and force him to quit on his stool at the end of the eighth round. De La Hoya then officially retired after the bout.


2) Muhammad Ali KO’s George Foreman

October 30, 1974

Stade du 20, Mai, Kinshasa

The late, great Muhammad Ali — also known as ‘The Greatest’ — traveled all the way to Kinshasa to face the destructive fists of “Big” George Foreman in a bout that would later be remembered as the “Rumble in the Jungle”.

At the time, Foreman was considered an absolute beast of a man, having absolutely obliterated top-ranked opponents Joe Frazier and Ken Norton in his previous contests. Many fans felt Ali would then, in turn, suffer the same fate as his peers. Foreman was simply too big and too strong.

Although Ali was expected to try to use his speed, length, and craftiness to avoid Foreman’s power, he employed a now very famous technique that would earn him the upset victory. Ali introduced the world to the “rope-a-dope”, luring Foreman into exchanges along the ropes, allowing Foreman to unload his strongest punches.

By the eighth round, Foreman was absolutely exhausted, and Ali finished him off from there. It was an unbelievable upset at the time and a win that some consider the best of Ali’s illustrious career.


1) James “Buster” Douglas KO’s Mike Tyson

February 11, 1990

Tokyo Dome, Tokyo, Japan

Mike Tyson was known in the late 1980’s and the early 90’s as the ‘Baddest Man on the Planet’. He was the heavyweight champion of the world, and he was virtually untouchable.

Behind a relentless offensive, fearsome uppercuts and concussive hooks, Tyson made a habit of destroying any man he was put in the ring with. So when he met heavy underdog James “Buster” Douglas at the Tokyo Dome in 1990, a loss was certainly unexpected.

Douglas entered the bout a 42-1 underdog, taking on the undisputed titleholder — a knockout artist that had no equal. He was also a journeyman with an unremarkable record.

Little did he know before the bout, however, that it would turn out to be the definitive moment in his career. Unlike the majority of Tyson’s previous opponents, Douglas refused to cower in his presence and instead took the fight right to Tyson. He eventually won via 10th round knockout, punishing Tyson for the entire contest with a fervent display of offense.

Tyson could not beat the count and Douglas scored perhaps the biggest upset in the history of boxing.

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