Biggest betting coups of all time

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Some have tried to beat the system for as long as people have been gambling. And while some have failed miserably, others have struck it lucky and walked away with huge winnings. This article take a peek at some of the biggest betting coups of all time!

The New York Yankees win the World Series

The New York Yankees have been one of the most successful teams in baseball history, winning 27 World Series titles. As a result, they are also one of the most popular betting targets for sports bettors.

The Yankees have been involved in some of the biggest betting coups in history. In 1998, a group of professional gamblers placed a $1 million bet on the Yankees to win the World Series. The bet paid off when the Yankees defeated the San Diego Padres in the World Series.

In 2001, another group of professional gamblers placed a $3 million bet on the Yankees to win the World Series. This bet also paid off when the Yankees defeated the Arizona Diamondbacks in the World Series.

These two bets are among the most significant betting coups in history. They both involved professional gamblers with deep pockets and a lot of confidence in the Yankees.

The Miracle on Ice

The United States Men’s National Team’s victory over the Soviet Union in the 1980 Winter Olympics is often viewed as one of the greatest moments in American sports history. The team, made up of amateur and collegiate players, upset a Soviet team that had dominated previous Olympic Games.

The game was also a big moment for sports betting. The Americans were heavy underdogs against the Soviets, and most bookmakers refused even to take bets on the game. Those who did take wagers generally had the Soviets as -1,000 favourites (meaning you’d have to bet $1,000 to win $100).

But a few brave bettors believed in the Americans and placed large wagers on them to win. Then, when the United States pulled off the upset, these bettors cashed in big time.

Billy Walters, a famous bettor, placed $3.5 million in bets on the U.S. team at Las Vegas casinos. He reportedly won more than $11 million on the game, which is still considered one of the biggest sports betting coups of all time.

The underdog Seattle Seahawks win a thrilling Super Bowl

The Seahawks win the Super Bowl in a close game, defeating the New England Patriots by a score of 24-23.

Seahawks quarterback Russell Wilson is named the Super Bowl MVP, completing 16 of 26 passes for 247 yards and three touchdowns. Seahawks running back Marshawn Lynch rushed for 102 yards and a touchdown on 24 carries.

It was undoubtedbly one of the most shocking upsets in sports history. The Seattle Seahawks, considered heavy underdogs, won the Super Bowl against the heavily favoured Denver Broncos. It was a stunning victory and one that will be remembered for years to come.

Leicester City wins the Premier League

It was a wild ride for Leicester City fans in the 2015/2016 season. From the team’s unlikely run at the top of the Premier League standings to their eventual victory. The Foxes started the season as relegation favourites but defied all expectations to finish as champions. Their journey is incredible, and their story deserves to be told.

Leicester City’s improbable title win is now etched in English footballing history. The Foxes defied the odds to pip Tottenham Hotspur to the Premier League crown and became the first team from the Midlands club in over 50 years to lift the trophy. Tottenham Hotspur dominated much of the season, but Leicester City found a way to win thanks to some shrewd signings, guided by manager Claudio Ranieri.

At the start of the season, Leicester an astounding 5000-1. To put it in perspective, the odds of aliens landing on Earth were significantly lower. So, while very few grabbed that offer, the ones that managed to pull off a legendary coup.

And while Leicester City’s win may have come as a surprise to some, it’s certainly not the biggest betting coup of all time.

That title still belongs to Joseph “The Fat Man” Lindo, who famously won $640,000 after correctly picking all 13 of that week’s NFL games in 1974. But Leicester City’s win is certainly up there and will go down in history as one of the biggest betting upsets ever.

Michael Jordan’s Flu Game

It’s widely considered one of basketball’s most outstanding individual performances. It was 1997 NBA Finals, Game 5, when Michael Jordan played through flu-like symptoms to lead the Chicago Bulls to victory over the Utah Jazz. His performance was miraculous, as he scored 38 points and hit the game-winning shot with just seconds remaining.

But another story to this game is not as well known. According to legend, Jordan was so sick that he couldn’t even bet on himself to win the game. But one sharp-eyed gambler saw an opportunity and placed a big bet on the Bulls. As a result, that lucky gambler won a small fortune when the Bulls pulled off the upset.

This shows that sometimes, the biggest betting coups are the ones you don’t see coming. So keep your eyes open, and you might win big as this lucky gambler did.

Monty’s Pass betting coup 2003 Grand National

In 2003, a horse named Monty’s Pass won the Grand National, one of the biggest horse racing events in the world. The winnings from this event are usually huge, and Monty’s Pass was no exception.

A group of horseracing enthusiast and gamblers owned the gelding, which faced one of the strongest Grand National fields in history. The connections began punting the horse at 40-1 and the public followed suit, until the odds crashed to 16-1 at the off. The tenacious 6 year old bay travelled well throughout ans won with ease. They put their money where their mouth was and reaped the rewards

This type of betting coup is tough to pull off, and as a result, Monty’s Pass remains one of the biggest betting coups of all time.

Son Of Flick betting coup 2012 Coral Cup

The Son Of Flick betting coup was a massive upset in the horse racing world. The race was the Coral Cup at the Cheltenham Festival in England. Son Of Flick was a huge underdog, but he won the race by a massive margin.

This was a massive shock to the bookmakers, who initially had Son Of flick at odds of 100-1. The punters who backed him into 16-1 won a fortune!

The Son Of flick betting coup is just one of many famous betting coups that have taken place over the years. Others include the Aintree Grand National, the Epsom Derby and the Prix de l’Arc de Triomphe.

If you fancy your chances at backing a big winner, keep an eye out for the next big betting coup!


As we’ve seen, there have been some pretty big betting coups throughout history. From the Jockey Club fixing races in the 19th century to Sonny Liston taking a dive in his fight against Muhammad Ali, there are plenty of examples of how gamblers have managed to rig the system in their favour. While it’s certainly not advisable to try and cheat the system, it’s always fascinating to look back at these stories and see how they unfolded.

The biggest betting coups show us that anything is possible if you’re willing to take a risk. From the famous case of the “Rogue Trader” who took on the Bank of England to more recent stories of gamblers who have beaten the odds, these stories are a reminder that sometimes, gambling can pay off big time. So if you’re feeling lucky, why not plan a coup? You might just stroll away with a life-changing win.