5 of The Largest Sports Betting Wins in History

In 5 of the largest sports betting wins in history we revisit some of the biggest bets that have been won all over the world.

Jack Hartman
July 29, 2021
July 29, 2021

Often as bettors, we are torn between placing bets that can steadily grow an account or placing bets that offer returns so big it could potentially change our lives. For many of us we will never hit that big bet but for some they have hit the jackpot. Below we revisit some of the biggest bets that have been won all over the world.

1. Leicester City Premier League Winners - 5000/1


One of the greatest fairytales in all of sports was when Leicester City won the Premier League back in2016. Narrowly avoiding relegation in 2015, it was fair to say that for many pundits and probably those within the team themselves, Leicester's main goal for the 2016 season would have been ensuring Premier League survival. One of the pre-season favourites to get relegated, Leicester were priced at a whopping 5000/1 to win the 2016 Premier League title.

Starting the 2015/2016 season well, Leicester would go onto accrue 11 points from the first 15 available - further wins against title contenders Liverpool, Chelsea,Man City and Tottenham saw Leicester climb all the way to top spot with just 10matches to go. As the season entered its final stages, many thought Leicester would eventually succumb to the pressure, but instead the Foxes went on a stunning run, winning 7 out of their last 10, drawing the remaining 3 matches, sauntering across the finishing line and claiming a first historic title win.

Many super-fans backed Leicester at the start of the season where they took full advantage of the 5000/1 odds that the book makers were offering. Even despite Leicester’s fast start, the bookmakers took no notice of their steady rise to the top of the table and even a few months into the season were continuing to offer big odds for Leicester winning the title, with some punters being able to back the Foxes at 500/1. It is these bets that saw the bookies take the biggest hit with bookmakers paying out well over£20 million for Leicester’s shock title win.

The bookies have certainly learnt their lesson, as nowadays punters looking to place a bet on relegation tipped teams to win the title won’t get anywhere near odds of 5000/1. For example, for this upcoming Premier League season, a bet on recently promoted Watford will only stretch as far as 1000/1.

Leicester’s title win not only shocked the football world, but also redefined how football markets are now evaluated.


2. £2 turned into £1.45 million


Some of the biggest bets in sports are often laid on horse racing. Offering tremendous odds and the opportunity for combining bets into many different multiples, there have been many instances where punters have won big.

In 2008, Fred Caggs a 60-year-old fertilizer salesman won £1 million pounds off a tiny 50p bet where he successfully predicted 8 selections. But there is perhaps no finer example of someone turning a small bet into a small fortune than Steve Whitely.

In 2011, Whitely a 61 year old heating engineer placed a £2 bet on 6 horses to win, with one of his selections having not won a race in 28 attempts! Betting on horses called Mr. Bennett, Semicolon, Black Phantom, Lupita, Lundy Sky, and Ammunition, Whitely’s successful 6 selections would go onto yield an overall return of £1.45 million, making this one of the most successful bets of all time.

3. Floyd Mayweather’s $5.9 million bet

Floyd ‘Money’ Mayweather is one of sports most infamous bettors often posting social media posts displaying his ridiculously large bets. Ranging across multiple sports, Mayweather has placed bets on the NBA, NFL and boxing.

However his biggest bet was placed in 2013 when he placed a bet of $5.9million on the Miami Heat to overcome the Indiana Pacers in game 7 of theNBA playoffs. Mayweather backed the Heat to overcome a -7 point difference. The bet was so big that Mayweather had to place the bet across nine different bookmakers. It was money well invested as the Heat would go onto win 99-76, netting Mayweather a return of well over $6 million dollars.

4. The biggest baseball bet in history

This article couldn’t have been published at a better time, recently inJune 2021, a historic bet was placed on the Houston Astro’s to win baseball’sWorld Series.

The bet placed by successful American businessman Jim McIngvale otherwise known as ‘Mattress Mack’ totals $2 million dollars where if successful, his bet would return a total of $20 million.

The Astro’s are currently trading at 10/1 to win the World Series and they are currently leading the American League with Vegas making the Astro’s the 6th favourites to win it all. Placing the bet with William Hill, William Hill have stated that the possible $22 million ticket would be the biggest reported payout in U.S. sports betting history.

"This is a potentially historic bet, and it’s one that we love to take,

"We pride ourselves on our flexible limits in our sportsbooks and sports betting apps. This wager certainly makes baseball season a little more excitingfor us, and we’re looking forward to seeing how that plays out.’


5. Billy Walters wins big by backing the Saints


One of sports most famous gamblers is American businessman Billy Walters. Walters moved to Las Vegas in his early teens and started up his own sports betting company, becoming one of the first pioneers in the industry to use algorithms and statistical modelling to place bets. In his early days it was reported that Walters was often winning upwards of $15 million dollars a year through successful bets.

Walters biggest bet came back in 2010, when he backed the New Orleans Saints to beat the Indianapolis Colts in Super Bowl XLIV. The Saints entered the Super Bowl match-up as heavy underdogs to the Peyton Manning led Colts. For many, Super Bowl XLIV was Manning’s time, and many were crowning him Super Bowl MVP before a ball had even been snapped.

Walterstook a different view and placed one of sports biggest wagers, $3.5 million on the Saints to cause an upset. The game started in a fashion that everyone was expecting with the high-powered offense of the Colts bounding into an early ten-point lead.

Trailing10 – 6 at the half, the Saints kicked off the second period and produced one of the greatest Super Bowl moments we have ever seen. Needing a spark, Saints Head Coach Sean Peyton called for an onside kick. With the Colts expecting Manning to get the opportunity of starting the second half with possession, they were completely caught unawares by Peyton’s gutsy call. The Saints were successful with the kick and would go onto win the game comfortably 31 – 17, outscoring the Colts 31 – 7 through the final three quarters.

Nobody knows how much Walters won off the back of the Saints victory but due to theSaints status as underdogs it is expected that the total could have been well over $8 million dollars, which would make this bet one of the biggest ever recorded.

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