The Best Betting Wins of All Time

Which Teams Helped Bettors Cash the Biggest Tickets?

Last weekend’s Kentucky Derby was one for the ages, as 80:1 longshot Rich Strike entered the race on Friday morning and won the Run for the Roses less than 36 hours later.

Rich Strike joined the Miracle on Ice, Buster Douglas, and others in the conversation for the greatest sports upset of all time.

So let’s take a look at the biggest betting upsets of all time. Which teams cashed the biggest tickets for the bettors who trusted them?

Biggest Stanley Cup Upset: 2006 Carolina Hurricanes (60:1 odds)

The 2005-2006 NHL season was always going to be unpredictable, coming off the lockout that cancelled the previous campaign.

Sure enough, just about no one predicted the upstart Hurricanes led by rookie goaltender Cam Ward, would capture Lord Stanley’s Cup. But they did just that, upsetting heavily favored Buffalo in the Eastern Conference Finals before upending their fellow longshots, the Edmonton Oilers, to claim the unlikeliest Stanley Cup victory in the NHL’s long history.

Biggest World Series Upset: 1991 Minnesota Twins (80:1 odds)

It’s surprising the Twins’ odds were as high as they were, with several players remaining from a team that had won Major League Baseball’s biggest prize just four years earlier.

The early 1990s were controlled by some dominant teams in baseball, and the Twins weren’t seen as one of them. In fact, the eventual 1991 champions would prove to be one-year wonders, as the team would miss the playoffs the following season before embarking on an eight-year run without a winning record.

But for that magical 1991 season, not only did Minnesota win, they did so in spectacular fashion. After upsetting Toronto in the American League Championship Series, then played Atlanta to a standstill in one of the best World Series ever. Kirby Puckett’s game-winning home run in game 6 made Jack Morris’ ten-inning, complete-game shutout in game 7 possible. Minnesota won the title in extra innings over the Braves, who would become baseball’s “team of the 1990s.”

Biggest Super Bowl Upset: 1999 St. Louis Rams (150:1 odds)

You have to think the oddsmakers regretted this one quickly. After all, the Rams had four eventual Hall of Famers on the offense alone, including Isaac Bruce, Marshall Faulk, and Orlando Pace.

But it was the fourth Hall of Famer, quarterback Kurt Warner, who created the magical 1999 season in St. Louis. Forced into duty after Trent Green’s season-ending injury, the then-unknown Warner took the NFL by storm, throwing for 4,356 yards and 41 touchdowns as a first-year starter. The Rams held off the Vikings and Buccaneers in the playoffs before defeating the Tennessee Titans for the franchise’s first Super Bowl championship.

The out-of-nowhere season spurred Warner’s storied career, later memorialized in a Disney movie, and a huge victory for the few bettors who picked St. Louis. But it still pales in comparison to the greatest underdogs…

Sports’ Biggest Upset: Leicester City F.C. (2016 Premier league, 5,000:1 odds)

Just look at that number – 5,000:1 odds. More than 60 times as unlikely as Rich Strike’s Derby win, more than 30 times as unlikely as the 1999 Rams. There was NO ONE choosing Leicester City at the start of the 2015-2016 English Premier League season.

To put the upset in perspective: According to ESPN, English bookmaker William Hill made odds on unlikely world events at the time, and they had the odds of Elvis Presley being found alive – in 2016, mind you – at the same 5,000:1 likelihood as a Leicester City Premiership title.

How did it happen? Well, it was a down year for traditional powers like Manchester United, Chelsea, and Arsenal – but Leicester City weren’t expected to be the team to benefit. They were breaking in new coach Claudio Ranieri and narrowly escaped relegation the previous season.

Striker Jamie Vardy had a particularly fruitful breakout year, pushing the squad to the top of the league early before a Boxing Day loss to Liverpool dropped them from first place.

But Leicester City would return to first place, beating Aston Villa a few weeks later, and would not relinquish the top spot again. They actually won the title somewhat easily, clinching top honors with two games still remaining on their schedule.

It didn’t ignite a dynasty; in fact, a pair of fifth-place finishes is the best they’ve mustered in the years since. But the 2015-2016 Leicester City season is proof positive that in the world of sports – and sports wagering – anything is possible.

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