Greatest Underdog Stories in Boxing History

17 February 2025

Boxing is a sport where anything can happen. It’s a primal test of will, skill, and heart. But when the odds are stacked against you, when the world thinks you have no shot, that’s when the most unforgettable moments happen. The underdog stories. The tales where fighters defy all expectations, shock the world, and carve their names into the annals of boxing history. These are the moments that remind us why we love the sport so much.

In this article, we're going to dive into some of the greatest underdog stories in boxing history. So, buckle up, because these stories are filled with grit, determination, and a whole lot of heart.

1. Buster Douglas vs. Mike Tyson (1990)

When you talk about underdog stories in boxing, this one tops the list. By 1990, Mike Tyson was an absolute wrecking machine. He was undefeated, the undisputed heavyweight champion, and knocking out opponents like it was just another day in the office. Tyson wasn’t just a fighter; he was a force of nature. Most people thought he was unbeatable.

Enter James "Buster" Douglas.

Douglas wasn't exactly a household name. He was a solid fighter but had never been considered elite. And on top of that, 42-to-1 odds were against him. Nobody – and I mean nobody – gave him a chance when he stepped into the ring with Tyson in Tokyo on February 11, 1990.

But something strange happened that night. Tyson wasn’t his usual self. He seemed out of shape and maybe even a little disinterested. Douglas, on the other hand, had trained like a man possessed. He came out ready to fight.

And fight he did.

In the tenth round, Douglas landed a vicious uppercut followed by a flurry of punches that sent Tyson crashing down. The world was in shock. Tyson had been knocked out, and Buster Douglas had done the impossible.

Douglas' victory remains one of the most iconic upsets in sports history. It was a reminder that, in boxing, anything can happen. Never count out the underdog.

Key Takeaway:

This fight showed that even the most dominant fighters can fall, and it taught us to never underestimate heart and determination.

2. Muhammad Ali vs. George Foreman (1974 - "The Rumble in the Jungle")

George Foreman was a monster in 1974. He had just demolished Joe Frazier and Ken Norton – two fighters who had given Muhammad Ali trouble in the past. Foreman was younger, stronger, and hit like a freight train.

Most people thought this fight would be the end of Ali’s career. At 32, many considered Ali to be past his prime, and the odds were stacked against him.

But if there's one thing you should know about Muhammad Ali, it’s that he thrived when people doubted him.

The fight took place in Zaire (now the Democratic Republic of the Congo), and Ali had a plan that no one – especially Foreman – saw coming: the now-famous "rope-a-dope" strategy. Ali leaned against the ropes, absorbing Foreman’s brutal punches, conserving his energy, and waiting for Foreman to tire himself out.

By the eighth round, Foreman was exhausted. Ali saw his moment and unleashed a series of punches that sent Foreman down to the canvas. Just like that, Ali had pulled off one of the greatest upsets in boxing history.

Ali’s victory wasn’t just about boxing. It was about strategy, resilience, and proving the doubters wrong. The "Rumble in the Jungle" is still remembered as one of the most legendary moments in sports.

Key Takeaway:

Ali’s win showed that smarts and strategy can beat brute force. It's not always about who hits the hardest – sometimes it’s about who thinks the sharpest.

3. Hasim Rahman vs. Lennox Lewis (2001)

Lennox Lewis was the undisputed heavyweight champion in 2001 and considered one of the best heavyweights of his era. Hasim Rahman, on the other hand, was seen as just another challenger. A good fighter, sure, but not in the same league as Lewis.

The fight was scheduled in South Africa, and many believed that Lewis, despite his talent, had taken the fight a little too lightly. He spent more time filming a movie (he had a cameo in "Ocean's Eleven") than preparing for Rahman.

Rahman, however, was laser-focused. In the fifth round, he landed a massive right hand that put Lewis on the mat. The boxing world was stunned. Rahman had just dethroned the heavyweight king.

Although Lewis would get his revenge in a rematch later that year, Rahman’s victory remains one of the most shocking upsets in heavyweight boxing.

Key Takeaway:

Complacency can be a fighter’s worst enemy. No matter how talented or dominant you are, you can never underestimate your opponent.

4. Andy Ruiz Jr. vs. Anthony Joshua (2019)

When Andy Ruiz Jr. stepped in to replace Jarrell Miller (who failed a drug test) for a fight against Anthony Joshua, nobody gave him a second thought. Ruiz didn’t look like the typical heavyweight contender. He didn’t have the chiseled physique that Joshua boasted. In fact, some people even mocked Ruiz’s appearance.

But here’s the thing: looks can be deceiving.

On June 1, 2019, at Madison Square Garden, Joshua – the heavily favored unified heavyweight champion – came face-to-face with Ruiz. Most thought it would be a walk in the park for Joshua, but Ruiz had other plans.

After Joshua knocked Ruiz down in the third round, it seemed like the script was going according to plan. But then Ruiz got up and started swinging. He knocked Joshua down not once, not twice, but four times before the fight was stopped in the seventh round. Ruiz had shocked the world and became the first-ever Mexican heavyweight champion.

It was a reminder that boxing isn’t about who looks the part; it’s about who fights the part.

Key Takeaway:

You can’t judge a book by its cover. Andy Ruiz proved that heart, skill, and determination can overcome any physical appearance or preconceived notion.

5. Leon Spinks vs. Muhammad Ali (1978)

Muhammad Ali was a living legend by 1978. He was the reigning heavyweight champion and had already established himself as one of the greatest boxers of all time. His opponent, Leon Spinks, was a relative unknown with only seven professional fights under his belt.

The fight took place on February 15, 1978, and most people assumed it would be an easy win for Ali. But Spinks had other ideas.

Spinks fought with relentless pressure, never giving Ali a moment to breathe. After 15 rounds, Spinks was awarded a split decision victory, and the world was stunned. Ali had been beaten by a virtual novice.

Although Ali would win the rematch later that year, Spinks' victory remains one of the biggest upsets in boxing.

Key Takeaway:

Even the greatest can fall when faced with relentless determination and hunger.

6. Manny Pacquiao vs. Lehlohonolo Ledwaba (2001)

Before Manny Pacquiao became a global boxing icon, he was just another scrappy fighter from the Philippines looking for a break. In 2001, he got his chance when he stepped in as a late replacement to fight Lehlohonolo Ledwaba for the IBF super bantamweight title.

Ledwaba was the champion, and Pacquiao was relatively unknown outside of the Philippines. But that night, Pacquiao introduced himself to the world. He overwhelmed Ledwaba with his speed, power, and relentless pressure, eventually stopping him in the sixth round.

Pacquiao’s victory didn’t just earn him a world title – it kickstarted his legendary career, which would see him become one of the best pound-for-pound fighters in the history of the sport.

Key Takeaway:

Sometimes, all you need is one opportunity. Pacquiao’s win showed that when preparation meets opportunity, magic can happen.

Conclusion

Boxing is a sport that thrives on unpredictability. It's the ultimate stage for underdogs to rise, defy expectations, and leave an indelible mark on history. From Buster Douglas to Manny Pacquiao, these fighters showed us that heart, determination, and belief can overcome even the most insurmountable odds.

So, the next time you watch a fight, remember: the favorite might have the odds, but the underdog has the story.