7 Biggest Sports Gambling Upsets in History

St Louis Cardinals Celebrating Winning the 2011 World Series

Experienced bettors will tell you that there’s a lot of value in betting on the underdog. Any time you can win significantly more money than you risk, it’s a play worth considering.

While betting on your average underdog is something I’d recommend when the value is right, these underdogs aren’t average. In fact, the betting odds these underdogs overcame were so seemingly-insurmountable that no reasonable person would take the bet.

Some sports gamblers enjoy the thrill of potentially hitting a one-in-a-million that pays thousands (or more) on a longshot. These bets show that, while it’s highly unlikely, it does occasionally happen.

These bets will have you searching for the biggest underdogs and throwing a few dollars down, just in case.

1 – 2011 St Louis Cardinals: 999 to 1

Perhaps one of the most unlikely stories in MLB history was witnessed in 2011 when the Cardinals overcame 999 to 1 odds to win the World Series.

To get the full context of how the odds got this lopsided, I’ll back up. The Cardinals were 4.5 games behind the Braves for the Wild Card spot when Vegas listed the outlandish odds. To be clear, the odds were listed as a futures bet in which the Cardinals had to win the World Series.

The Braves imploded over the final 15 games of the season and the Cardinals went 11-4, which was good enough to claim the Wild Card spot. The fun was just getting started.

Fast forward to the World Series. One of the most memorable fall classics in baseball history, the St. Louis Cardinals somehow managed to overcome being down to their last strike multiple times in the series to win it in seven games.

Now, for the important question, did anyone actually take the 999 to 1 odds on the Cardinals winning the World Series? The answer is yes. One man pulled one over on the sportsbooks when he bet $250 on the Cardinals before their miracle run began, which resulted in a $250,000 payday. Who said baseball was boring?!

2 – Greatest Show on Turf: 300 to 1

The team who would later be known as “The Greatest Show on Turf” had a historically humble beginning.

For the St. Louis Rams, things looked bleak heading into the 1999 season after suffering a run of terrible seasons throughout the early 1990s. Before the first kickoff of the season, their big offseason signing QB Trent Green suffered an injury that would keep him out the entire season. When you think about it, 300 to 1 actually seemed pretty reasonable.

Nevertheless, the Rams persisted. With the lowest of expectations, they outperformed even the most optimistic fans by winning their division for the first time since 1985. Not only that, but they finished the regular season with a 13-3 record and became one of only four teams in NFL history to score 30 or more points 12 times in a single season.

On the back of off-the-street quarterback Kurt Warner, who finished as regular season and Super Bowl MVP, the Rams defeated the Titans in Super Bowl XXXIV to claim the title as longest shot to ever win it all.

3 – Miracle on Ice: 1,000 to 1

While you’re probably familiar with the story, the betting odds really help to see how big of an underdog the Men’s U.S. Hockey team was in the 1980 Winter Olympics.

In 1980, Olympians from the US were amateur athletes competing for the love of the game. The USSR’s juggernaut hockey team was an international power and a foregone conclusion to take home the gold at the winter games.

As you probably learned in your dorm hall freshman year, when college kids band together, they can do some pretty amazing things. In this case, it was winning a gold medal against a country we were in the midst of a cold war with at the time.

At 1,000 to 1, if you had bet on the stars and stripes to win it all, you’d be celebrating with all the fireworks you could buy.

4 – Leicester City: 5,000 to 1

The English Premier League features internationally-known clubs like Manchester United, Liverpool, and Chelsea. In a league full of powerhouses, Leicester City was less than just an afterthought, they were at “thousands” to 1 odds to win.

One fan decided to take the risk and put down roughly $60 USD (the bet was made in England). Most bettors would chalk that up as a waste of mon, but that’s why they play the games.

At the end of the season, the most unlikely EPL underdog story was capped off, as Leicester City took home the title and a handful of lucky gamblers took home a whole lot of cash.

5 – Ben Curtis: 300 to 1

Ben Curtis was still finding his footing in professional golf when he entered the British Open in 2003. As the world’s 396th ranked player, nobody gave him much of a chance to make any noise in the tournament. In fact, this was his very first time playing in a major.

Bookmakers placed odds at 300 to 1 on him winning the cup, and I haven’t been able to find any evidence of anyone actually taking the bet. Nobody can blame the public for passing that one up.

The interesting thing about Curtis’ weekend heroics is that, even entering Sunday in a five-way tie, he still only had 40 to 1 odds to win.

You can probably guess how it turned out. He needed a little help from Thomas Bjorn, who went +4 on the final four holes, but Curtis hoisted the trophy when it was all said and done. That would go on to be the only major Curtis would win, but the story to go with it almost makes it worth two.

6 – Cricket Conspiracy: 500 to 1

First, there was the Black Sox scandal that changed baseball forever. Several decades later, there was the England vs. Australia cricket conspiracy.

This bet wasn’t a longshot from the start, but in 1981, England found themselves down 18 runs in a cricket match against Australia. The most interesting part of what happened next wasn’t even the comeback.

Yes, the Brits did come back to win, but the sportsbooks revealed a pretty sketchy piece of information. It turned out, two Australian players had placed bets and won a total of roughly $8,500 USD on the play.

The pair did get fined by the Australian Cricket Board and probably didn’t win any new teammates. But at the end of the day, no serious consequences were ever laid on the duo.

7 – Douglas v. Tyson: 42 to 1

Mike Tyson had a 37-0 (with 33 knockouts) reputation to uphold when he faced off against Buster Douglas in a 1990 fight in Tokyo. Nobody gave Douglas much of a chance, but with the death of his mother fresh on his mind, the motivation gave him a boost the books didn’t account for.

Douglas controlled the fight in the early going but Tyson responded. The undefeated legend knocked down Douglas in the eighth round, but Douglas eventually laid the crushing blow. In the 10th round, against all odds (okay at 42 to 1 odds), he won the fight.

If you’re thinking that 42 to 1 doesn’t compare to the other odds above, consider this—most sportsbooks wouldn’t even offer a bet on the fight. We can’t imagine the one Vegas casino that did accept bets on the bout probably didn’t receive much action on the underdog.


Where some people see a waste of money, others see amazing value. Anytime there’s a contest with longshot odds, you can bet (no pun intended) some crazy gamblers will go chasing the big win. This article proves that, occasionally, it can pay out.

Tim Johnson / Author

Tim has been a sports fan for as long as he can remember. The Vermont native has lived in Las Vegas for the last two decades, and he uses his experience in the industry to try and give readers the best possible advice when it comes to betting on sports. Football is Tim’s primary area of expertise, but he also dabbles in other sports like horse racing and basketball. Tim uses his wealth of knowledge to try and make the reader a better bettor.