Biggest Underdog Wins in Sports Betting History

There’s something downright magical about a long-shot bet that actually pays off. You put a few bucks on a team or athlete no one believes in, and suddenly, you’re sitting on a pile of cash while the sports world scratches its head in disbelief. 

In a sporting event, the underdog is a player or team that, the odds say, has practically no chance. Think of a David versus Goliath scenario, except there’s a paycheck at the end. We’re going to dive into some of the betting’s craziest underdog wins where courageous players turned pennies into life-changing wins. Get set for remarkable stories that will motivate you to put money on the underdog.

What Is an Underdog, and Why Do We Bet on Them?

In betting, odds help you know who’s likely to win and who’s likely to crash and burn. A long-shot bet is a way of betting on the underdog with unbelievably high odds because the bookmakers believe they will lose. If you bet on a team with 5000 to 1 odds, you win $5,000 for every dollar you bet if they win. It’s a tiny chance, but the payoff is massive. So why do people do it? It’s simple.

• Getting to cheer for the impossible feels like joining a secret, exclusive club. You will be cheering for the team everyone else has written off.
• A five-dollar bet could become a new car or even a new house if luck is on your side.
• Stories of miracle wins that last forever: The legendary wins stick around and get told over beers for a long time. 

It’s a gamble, sure, but when it hits, it’s pure gold.

Top Biggest Underdog Wins in Sports Betting History

These five amazing underdog victories turned little bets into major news stories.

Leicester City Wins the Premier League (2015–16)

Sport: Soccer (Football)

Event and Date: In May 2016, Leicester City became Premier League champions, having never won the title before.

Odds: 5000-to-1

Bet: Some bettors turned £5 bets into six-figure payouts, including a man who made £72,000 from his wager. 

Leicester City, a scrappy football club, began the season as favorites for relegation. They surprised everyone by winning the Premier League by 10 points with a budget far smaller than that of the top six Premier League teams.

The bookmakers predicted that an Elvis sighting was more likely than the Leicester City football team winning the Premier League. It’s still the ultimate Cinderella story in sports. (sources: BBC Sport, TheLines.com)

Buster Douglas Defeats Mike Tyson (1990)

Sport: Boxing

Event and Date: Heavyweight boxing title fight on February 11, 1990

Odds: 42-to-1 odds

Bet: One lucky bettor converted a $1000 wager into a $37000 payout

Mike Tyson was the undisputed champion, with 37 victories and 0 defeats, 33 of which were cold knockouts. Buster Douglas, an up-and-coming boxer with no accolades, landed a 10th-round knockout that floored Tyson and the betting world in Tokyo, Japan. Tyson was regarded as a boxing god, so losing to a 42-to-1 to a nobody was unthinkable. (source:SportsOddsHistory.com)

Rich Strike Wins the Kentucky Derby (2022)

Sport: Horse Racing

Event and Date: May 7, 2022, Kentucky Derby

Odds: 80-to-1

Bet: One small $10 bet paid $800

Rich Strike was not even supposed to race. He only entered the race after another horse withdrew at the last moment. Then he won by seven lengths. At Churchill Downs, an unknown horse defeated well-bred favorites, which surprised those who enjoy betting and horse racing. (source:TheLines.com)

Greece Wins UEFA Euro 2004

Sport: Soccer (Football)

Event and Date: UEFA Euro Championship, 4th July 2004

Odds: 80-to-1 to 150-to-1

Bet: Some persons who placed a bet worth $100 at 150-to-1 won $15,000

Greece, a dwarf in the hulking European soccer world, took on giants like Portugal and Spain. They put up one of the best defense displays, shutting down world-class attackers. They would not let up until the final whistle where they secured a 1-0 victory against the host team. This was one of the biggest upsets in the football world. (sources: SportsOddsHistory.com, TheLines.com)

Richard Hopkins’ Lewis Hamilton Bet

Sport: Formula 1 Racing

Event and Date: Hamilton’s F1 record-breaking wins, 2007–2008

Odds: Up to 1500-to-1 combined

Bet: £350 across bets, paid out £165,000

Richard Hopkins spotted a young Lewis Hamilton karting and placed a significant bet: £200 he'd win F1 before turning 23, £100 before 25, along with a combo bet. Hamilton really came through here and won in 2007 and 2008. It was bonkers to bet on a kid to dominate a cutthroat sport only a few years later. It was indeed a next-level vision. (source:SportsOddsHistory.com)

Why These Stories Inspire

Everyone loves a good underdog story. These types of wins aren’t only about money but also proof that anything is possible. A team that's not rated by the betting expert, a boxer that was out of his depth, or a horse that nobody picked rewriting the script suddenly becomes legendary. For fans of the game, it’s a feel-good story. For the betting man, it’s a reason to be bold. These moments show that nothing is guaranteed in sports, and that’s what makes it so captivating.

Tips for Betting on Underdogs Responsibly

Want to try your luck? Here’s how to do it without losing your head.

1. Make your stake an amount you can afford to lose. A $5 flyer won't do you much harm if it doesn't come off.
2. Take the time to explore deeply: Pay attention to injuries, momentum shifts, and those often-missed statistics—discover the subtle advantage.  
3. Avoid betting blindly on insane odds: 1-in-5000 sounds good, but the fact is that it is a long shot.
4. Play it safe: Establish a budget and adhere to it. Also, avoid wagering essential funds like rent money.

Remember to always bet responsibly and within your means

If you ever feel that your betting is getting out of hand, please visit our Responsible Gambling page for support and resources. Play smart, and you might just get lucky!

Conclusion

Upset victories like Leicester's miracle or Douglas knocking out Tyson show that in sports, nothing is impossible—and often isn’t. These tales, however crazy, speak to us of guts, luck, and taking a bet on an outsider! Ever hit a big underdog bet yourself? We’d love to hear about it—drop your story on our Join Us page or check out our Careers page to contribute and maybe even get paid. Your winning moment could be the next legend we feature!