Looking Back at the Biggest Upset in Sports Betting History One Decade Later

There’s no better feeling than betting on a big underdog only to watch them pull off the upset and cash a big ticket in the process. It doesn’t happen often, which is what makes the biggest upsets remain in our collective memory for years to come.

Here, we examine the biggest upset in sports betting history, a decade after it happened.

Leicester City Wins 2016 Premier League Title (5,000-1)

Bookmakers offered Leicester City at +500000 entering the 2015-16 Premier League season, giving The Foxes an implied probability of 0.02% (or 1 in 5,001) of pulling it off. Chelsea entered the campaign as the +160 betting favorite.

Many pundits expected The Foxes to be relegated from England’s top division after barely escaping that plight the previous season. Instead, they shocked the soccer world with the biggest upset in Premier League history.

Leicester City benefited from the stellar play of goaltender Kasper Schmeichel (pictured above in a 2016 match), who produced 15 clean sheets after playing in all 38 games. Jamie Vardy and Riyad Mahrez fueled Leicester City’s offense, scoring 24 and 17 goals, respectively.

Manager Claudio Ranieri guided The Foxes to 23 wins, 12 draws, and just three losses. Leicester City clinched its first Premier League title on May 2, 2016, when Tottenham Hotspur and Chelsea played to a 2-2 draw. With two games left to play, The Foxes enjoyed an unbeatable seven-point lead in the standings.

Bookmakers took it on the chin. At the time, Sky Bet noted that 128 people backed Leicester City at the highest price of 5,000-1. That led to a record payout of £4.6M.

“The unthinkable has become reality, and we’re facing paying out the sort of liability that you joke about at the start of the season,” Sky Bet’s Sandro Di Michele said. “We’re now bracing ourselves for more punters looking to get on long-price outright odds, but Leicester certainly won’t be 5,000-1 next season!”

A decade later, Leicester City has failed to win a second Premier League title. The Foxes have been relegated from the Premier League multiple times since, and most recently in April 2026, to League One after a 2-2 draw with Hull City.

Most Recent Premier League Winners & Championship Odds

As you’d probably guess, nobody has sniffed Leicester City’s long-shot odds in the ensuing decade. Here’s a look at the most recent winners and their odds courtesy of Sports Odds History.

Manchester City is the antithesis of Leicester City, winning five of its six recent titles as the odds-on favorite.

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 There’s no better feeling than betting on a big underdog only to watch them pull off the upset and cash a big ticket in the process. It doesn’t happen often, which is what makes the biggest upsets remain in our collective memory for years to come. Here, we examine the biggest upset in sports betting
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