Biggest Ever Sports Betting Upsets

There are few things more entertaining to a sports fan than the prospect of an underdog winning when no one expects it. And, for sports betting fans, these upsets can produce an impressive payout.

Sports betting customers often spend time looking for free sports bets, and what could be more satisfying than landing an unexpected winner at huge odds? Of course, big upsets don’t happen very often, which helps to explain why they are so memorable. They can come about because of good fortune or an all-time great sporting performance. Here are some of the biggest betting upsets of all time.

Leicester City – English Premier League 2015-16

The Premier League in England is one of those leagues where the cream always rises to the top. Only five teams have won the league since 2010: Manchester United, Manchester City, Chelsea, and Liverpool. And then, Leicester City won in 2016.

At the start of the season, Leicester City was a +500,000 underdog to win the Premier League. This is not surprising, given that they had nearly been relegated the year before. A Leicester City Premier League win wasn’t just unlikely; it was near-impossible. And yet, having made a strong start, they kept going, underestimated until they had built up a lead at the top of the table. By betting on them to win, one sports gambler was able to transform £100 into £200,000. It's difficult to overestimate the extent of this shock.

Miracle on Ice – 1980 Winter Olympics

The “Miracle on Ice” was an ice hockey game played in Lake Placid, New York, during the 1980 Winter Olympics, between the host the United States and the Soviet Union.

It's difficult to put into words how much of an underdog the American team was in this one. This was a one-in-a-thousand chance. A $100 bet on the squad would have resulted in a $100,000 total return.
Following their bronze-medal finish at Squaw Valley in 1960, Soviet teams were 27–1–1 (wins-losses-ties) in four Olympics, outscoring their opponents 175-44.

The United States team was thrashed 10-3 by the Soviets just days before the Olympics in Lake Placid. As a result, no one thought the hosts had a chance. The US team was behind 2-3 going into the third period of the game, yet scored two late goals to upset the Soviet team and win 4-3.

St. Louis Cardinals – 2011 World Series

The St. Louis Cardinals were not in great shape to win the World Series in 2011. They were 4 ½ games behind the Atlanta Braves for the National League Wild Card position, with only 15 games remaining in the regular season. As a result, Las Vegas sportsbooks had them pegged as a 999-1 underdog.

But, as is often the case in sports, the unexpected happened. In their final 15 games, the Cardinals went 11-4, while the Braves faltered. St. Louis advanced all the way to the World Series, where they defeated the Texas Rangers to win the series and pay out handsomely to those who wagered on them.

Rich Strike – Kentucky Derby 2022

In this year’s Kentucky Derby, Rich Strike was an 80 to 1 long shot. His pedigree, as well as his track performances, did not suggest that he had the stuff that Derby winners are made of.

For most of the race, he didn’t feature. In fact, he wasn’t mentioned by the announcers until extremely late in the contest. But, as the longshot horse barreled past the odds-on favorite down the final stretch, spectators, viewers, and announcers alike were stunned. The 148th Kentucky Derby at Churchill Downs will go down in sports history as one of the greatest upsets ever.

Buster Douglas v Mike Tyson – 1990

This fight took place at a time when Mike Tyson was at his peak: a warrior who frightened everyone who dared to oppose him. Tyson was 37-0 with 33 knockouts coming into this fight. He didn't simply win; he won decisively and quickly.

In contrast, Buster Douglas was an unheralded unknown. He was seven years older than Tyson and had four defeats on his resume. But, as the saying goes, everyone has a puncher's chance.

This bout, unlike most of Tyson's others, went all the way to the tenth round. Douglas was knocked down in the eighth round by a devastating uppercut from Tyson. But, at the ninth count, Douglas hauled himself to his feet. And he kept coming, landing a right punch on Tyson that stunned him. Douglas then landed a flurry of jabs and hooks that knocked Tyson to the ground, creating one of sport’s greatest shocks.