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10 Biggest Betting Wins: The Longest Odds To Have Ever Paid Off

 Leicester City winning the EPL is one of the longest odds & biggest betting wins in gambling

Whether you prefer to gamble in a renowned online casino or reputable land casino, odds play a part in every bet you make – they determine the size of your wins and your loses. 

From a 25,000-1 wager to a 50/50 gamble, we’ve picked ten of the biggest betting wins and longest odds that have ever come off. 

Gambler beats the odds on Dettori’s magnificent seven

1996 is rose-tinted for many sports fans – it’s the year of “three lions on a shirt” when football came home and so nearly stayed for another four years. 

But the European Championships isn’t the only significant sporting event of 96 – it’s also when Frankie Dettori beat some of the longest odds in sporting history, by riding all seven winning horses at Ascot. 

While Dettori started the day as one of the hot tips, the odds on him winning all seven races were insane – 25,095-1, to be precise. That didn’t sway Darren Yeats, who wagered £59 on Dettori’s magnificent seven. The result? £550,000 in Mr Yeats’ back pocket. 

Determined baseball fan sees their loyalty pay off 

It can be a thankless task being a sports fan, especially if you like to place a bet on your team. In 2011, one baseball fan made two $250 bets on the St. Louis Cardinals and boy did they repay his loyalty! 

The first bet was on the Cardinals making the World Series (500-1). Check. The second was on the Cardinals winning the World Series (999-1). Check as a result of their loyalty, that fan got one of the biggest bets wins ever seen – $375,000. 

Poker player wins a $340,000 at the golf course 

Erick Lindgren has won over $9,000,000 in his career as a professional poker player, claiming two World Poker Tour (WPT) titles and two World Series of Poker bracelets along the way. However, one of his biggest betting wins came on the golf course. 

In an era where Android online casinos allow you to make bets quickly and impersonally, the idea of wagers between peers feels like an afterthought in gambling. But Lindgren was bet by fellow poker pros that he couldn’t play four rounds of golf consecutively in one day, and do so in under 100 shots each time. 

Lindgren stepped up to the plate, met the terms of the bet and collected a cool $340,000 from pros that included the legendary Phi Ivey. While we don’t have the odds of the bet, we can be sure that Lindgren liked them! 

Sad story of the Tennis fan who didn’t live to see his bet win

Roger Federer is one of the greatest tennis players of all time – as the current Grand Slam winner record holder (20, and counting), he might say that he is the greatest. In 2003, Nick Newlife placed a bet on Federer’s greatness and the Swiss master delivered the results. 

After winning his first Wimbeldeon, Newlife wagered £1,520 on Federer winning six more All England Lawn Tennis Championships titles before 2019, at odds of 66-1. Federer won his seventh title in 2012, however, Newlife had sadly passed three years prior. But Newlife had made provisions for this in his will and his £101,840 was paid to Oxfam. 

Gary Lineker loses his bet as Leicester City smash the odds

Gary Lineker is possibly Leicester’s finest footballing son – he scored 95 goals in 194 games for his hometown club, became a World Cup hero for his nation, and now hosts the UK’s most enduring football show (Match of the Day). 

But Leicester might be happier with Lineker dropping his trousers on national TV than any of his goals. Why? Because it saw Lineker gladly lose a bet that Leicester City would win the English Premier League (EPL). 

Leicester City’s odds of winning the EPL in the 2015/16 season were 5,000-1 – to put that into context, it was a tenth as likely as Simon Cowell being named Prime Minister

With devoted fans of Leicester City placing bets on their team winning the EPL, there were some lucky people who claimed betting wins big enough to pay off their mortgages – a result they’ll be a lot happier with than seeing Lineker in his pants! 

The Suitcase Man makes a huge casino bet & wins big 

One of the biggest bets and wins in history came in 1980. This was after a Texan high-roller took advantage of the Binion's Horseshoe Casino’s policy of honouring any wager (irrespective of the amount), if it was their first bet. 

William Lee Bergstrom entered the casino with two suitcases – one was empty, the other contained $777,000. 

The Suitcase Man bet the $777,000 on Don't Pass in a game of crabs and doubled his money. And why is this great? Because in an age of Android online casinos, VR betting, and esports, it’s heartening to know that a brick and mortar casino still provides one of the most infamous tales in the history of gambling. 

A £0.30 bet at odds of 1,666,666-1 REALLY pays off 

One of the must-have features of any sports leaning online casino is the ability to place accumulator bets – it’s a way of securing a potentially huge betting win and one that caters to mobile casinos need for fluid gambling. 

However, before the notion of Android online casinos was an idea (let alone a reality), a sports fan placed a £0.30 bet accumulator at odds of 1,666,666-1 – spoiler alert, he won BIG! 

The bet was made by an unidentified fan on the outcome of a huge number of sporting events – the champions of the top five English football divisions, top three Scottish football leagues, Champions League winners, victorious cricket County Championship side, and Rugby Union champions. 

When the final bet came through, the punter scooped £500,000 from his £0.30 wager. 

One gambler really didn’t want Scotland to gain independence

In an era when data can swing an election, Android online casinos allow bets to be made on the move, and video technology has changed the world of sports, it’s rare that so much rides on a simple “yes” or “no” answer. In the case of one anonymous gambler, there was £900,000 riding on such a 50/50 odds scenario. 

In 2014, an anonymous better wagered £900,000 on there being a “no” in the vote for Scottish independence. The bet came through, netting the punter £193,000, but that’s not where the story ends. That same gambler bet their winnings on there being a hung parliament in the next UK general election. They lost the bet and with it their winnings. 

Tiger Woods’ 2018 Masters win turns tasty odds into a big win

In 2018, Tiger Woods was responsible for one of the greatest sporting achievements in modern history –  a year prior to the tournament he was ranked 1,199 in the world, while it was half a decade since he’d last enjoyed a serious victory. 

Tiger won the 2018 Tour Championship, but he didn’t stop there and (at least) one gambler was very grateful for his efforts. 

Tiger began the 2019 Masters with tasty odds of 14-1 (the same he was given to win the 2018 Tour Championship). A trader, James AdduciI, saw these as a great opportunity and used them to secure one of the biggest betting wins in history. 

Adduci decided to be “everything I had that I could afford to lose,” which amounted to a $85,000 bet on Tiger – the stakes were enormous. 

On April 14, 2019, Woods secured his victory, netting himself his first major in 11 years, 15th in total, and a win of $1,200,000 for Adduci. 

Sports betting legend makes huge bet on Super Bowl XLIV

Billy Walters is universally regarded as the most successful sports gambler in history, after enjoying a winning streak that lasted for over 30 years – Although his good fortune ran out in 2017, when he was found guilty of insider trading. But in 2010 his luck was still high and he used it to make a big win from Super Bowl XLIV. 

Walters used runners to place a huge bet on underdogs the New Orleans Saint. And the result? He won an estimated $3,500,000. 

While there may be wagered we’re unaware of that have longer odds and bigger wins, these are our favourite long-shot and big pot wins in the history of gambling. And the one we like the most? We can’t look past Leicester City’s fairytale win! 

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