Veteran punters know that when it comes to sports betting, the race is a marathon rather than a sprint. Successful players are the ones who are capable of beating the house edge over the long run and hope for the biggest winning bets.
Cashing in on a big winning bet is definitely refreshing and the success of the luckiest punters reverberates throughout the sports betting community.
There are plenty of shining examples out there, but below we’ll list the biggest betting wins in history, at land-based and online bookmakers.
Success stories have the merit of inspiring others and the Internet is full of such tales. The biggest betting companies have had their fair share of losses and were occasionally forced to pay some huge winnings. What helps these companies stand out from the crowd is their willingness to accept high bets and when the time comes, uphold their end of the deal.
The biggest bookmakers in the world accommodate high rollers and allow them to bet larger amounts at huge stakes and at the same time offering the highest payouts.
🥇 Best online bookmakers with the highest payouts 
Top 10 biggest winning bets in sports history
Sports betting has been a popular affair for decades and huge amounts were wagered over the years. The biggest bookmakers UK has to offer paid billions of dollars and significantly larger amounts were paid beyond borders. Some punters got lucky and won fortunes, while others came painfully close to cashing in and changing their lives. These are some of the most amazing stories of profitable football betting and a perennial source of inspiration for punters trying to figure out how to beat the bookies.
1. Billy Walters won a $3.5 million NFL bet
Before his unfortunate run-ins with the law, Billy Walters had a few memorable years. His biggest accomplishment was a bet on the New Orleans Saints to defeat the Indianapolis Colts in 2010. Back then the bookmakers’ withdrawal limits were much lower online, so he chose to bet locally. He wagered $3.5 million on the underdogs and he made history with one of the top biggest betting wins. Sadly for him, he was sentenced to 5 years in prison in 2017, but at least he can still brag about the biggest bet ever won.
2. Tiger Woods made James Adducci rich
The first name that comes to mind when we think about golf betting is Tiger Woods. He won some amazing tournaments in his career and spent a lot of time in the spotlight, sometimes for the wrong reasons. Not surprisingly, he is involved in one of the biggest winning bets, one placed in 2019 by James Adducci. The punter didn’t lose confidence in the star golfer who was struggling at that point. He was confident enough to bet $85,000 on his win at odds of 14/1 with William Hill to win a massive paycheck of $1.2 million.
3. Vegas Dave cashes in on Kansas City Royals
The infamous Vegas Dave is disliked by many for his attitude, but he can brag about one of the biggest betting wins. In 2015 he decided that the Kansas City Royals were capable of winning the NFL World Series. He was so convinced that he decided to place a major bet of more than $80,000 on this capable underdog. He was unable to find high-stakes betting sites willing to accept his futures bet, so he had to spread the amount among several operators. He was successful and walked away with $2.5 million.
4. Tayla Polia wins a massive NFL parlay
2015 was a great year for American football fans, but also a lucky punter betting on the NFL. Tayla Polia claimed one of the biggest winning bets in history by wagering on 15 matches. The odds were 20,000/1 so with a bet of a bit over five dollars she had the opportunity of winning $100,005. She wasn’t even a veteran punter, just an enthusiastic person hoping for the best when placing one of the world’s biggest winning bets. Her success is now an example for people on how to win football accumulators.
5. The biggest single bet odds in football history
Leicester’s amazing Premier League win remains one of the greatest accomplishments in the history of football. While it features on any list of legendary endeavors, it is also at the cornerstones of one of the biggest bets win in history based on the odds. In 2015 the odds were 5000/1 and a lucky punter was comfortable enough betting £100 on their title run. These were the maximum odds offered by legal betting sites and he chose to cash out his winnings sooner, so he claimed £200,000.
6. Holly Holm vs Ronda Rousey UFC match
Vegas Dave returned into the spotlight with one of the biggest sports betting wins when he wagered on the UFC. He decided to back the underdog Holly Holm against Ronda Rousey at odds of 11/1. An investment of $20,000 was nothing to frown upon, but the arrogant punter was happy to brag about it on social media. When the underdog prevailed, he ended up winning $220,000 and the fame he was hoping for. This remains one of the biggest UFC winning bets ever placed at any of the top 100 bookmakers.
7. Phil Mickelson wins on the Baltimore Ravens
The legendary golfer is known for his passion for sports betting and his willingness to wager larger sums. His name is tied to one of the biggest winning bets on Super Bowl when he wagered $20,000 on Baltimore. The Ravens ended up winning the Super Bowl at odds of 22/1 and Phil Mickelson was rewarded with a paycheck of $560,000. This remains one of the biggest winning bets of all time officially placed on an American football match.
8. Charles Barkley wins big on the New England Patriots
When trying to figure out what is the biggest bet ever won, one name frequently appears on the list of possible candidates. Charles Barkley made a fortune with his illustrious sports career, but he was just as successful as a punter. Bold enough to bet $500,000 on the New England Patriots to win the Super Bowl in 2002, he was lavishly rewarded. This remains one of the biggest wins in football history although he only cashed $800,000. His approach was intelligent and methodical, therefore the win wasn’t only luck.
9. A Louis Hamilton fac wins a major F1 bet
Formula One betting fell from grace in recent years because of the lopsided nature of the competition. Richard Hawkins was among the first to realize the immense potential of Lewis Hamilton and trusted him to win a Grand Prix before he turned 23. He placed a £200 bet placed early on at odds of 300/1 and another wager of the same magnitude at odds of 500/1 on him to become world champion. He only won £165,000 which isn’t one of the biggest UK winning bets, but the odds and confidence were amazing.
10. Massive NFL parlay win in Las Vegas
American punters who try to figure out how to win big on football bets focus exclusively on the NFL. A lot of money is wagered in local casinos and sports betting parlors, something that happened in 2017. At the MGM casino, an anonymous punter decided to wager on the Ravens, Patriots, Chiefs and Raiders. He invested $8500 at odds of nearly 30/1 and secured a paycheck of $250,000. This remains one of the biggest accumulator wins on the NFL and an amazing accomplishment for the Las Vegas bettor.
Top 3 biggest football bets ever won
Football is the most popular and easiest sport to bet on and the one that enjoys the best coverage at bookmakers. People enjoy adding multiple events on the same betting slip, so some of the biggest ever accumulator wins were on football games. If you look for the biggest bet ever won in football, you are likely to find it on this list.
1. Mr. Gibbs wins a fortune on Bayern Munich
2001 was a fantastic year for football fans and Mr. Gibbs was the luckiest punter of them all. With an insignificant wager of £0.30 he became a part of sports betting history with one of the biggest UK acca wins. He had a total of 15 matches on his betting slip and combined odds of 1,666,666. With winnings of £500,000, emotions were high when Bayern Munich’s goalkeeper defended Mauricio Pellegrino’s penalty kick. This produced the biggest football accumulator win ever and Gibbs was the main beneficiary.
2. Leicester’s huge single football bet winner
The biggest football bet win on a single event has to be the one on Leicester to win the Premier League. 2015 was the last time bookmakers offered odds of 5000/1 on an English team to win the top competition. Leigh Herbert of Leicester wagered £5 to win $25,000, while an anonymous punter wagered £50 on the same outcome. He decided to cash in his bet in March and only claimed £72,000 of the maximum payout of £250,000. He missed out on the biggest ever football win, but still walked away with a huge paycheck.
3. Huge win for anonymous punter from outcome
Turning £0.80 into £585,000 is a fantastic accomplishment and one that fully deserves to be mentioned here. This is one of the biggest football win ever and the shining example of how a bold accumulator can make you rich overnight. The player from Malta chose William Hill as the bookmaker of choice for the 19 match accumulator. The odds were a spectacular 683,738/1 and because all of his predictions were right, he was paid the full amount. The last match saw Liverpool defeat Chelsea in a nail biting affair.
Top 3 biggest horse racing bet wins
Horse racing used to be the most popular sport among punters and it continues to draw a lot of attention. Some of the biggest Cheltenham winning bets inspired others to persevere and try their luck. These are the top three biggest horse racing bets ever won, spanning over the course of three decades.
1. Fred Craggs wins a fortune with William Hill
The story of Fred Craggs who became a millionaire with a 50p bet is without a doubt one of the biggest betting wins in horse racing history. He chose to place an 8-fold accumulator with William Hill and won £1,000,000 with a small bet on his 60th birthday. What made the story even more exciting is that he didn’t even realize he became a millionaire. This is not only the biggest win ever made in horse racing, but also the top payout at a UK licensed bookmaker since gambling became legal in this country.
2. Anonymous punter wins £823,000
In 2017 a punter betting at Coral converted a £19 accumulator bet into a £823,000 paycheck. He decided to stay anonymous, but we know that he bet on horse races at the licensed UK bookmaker. This is not only one of the most successful attempts at beating the bookies on horse racing events, but also one of the best betting accumulators ever. We don’t know the name of the lucky winner, but his achievement is still worth celebrating as one of the biggest winning sports bets ever.
3. Darren Yates wins a fortune on Franki Dettori
Franki Dettori has set multiple records over his illustrious career, but one of the biggest accomplishments came in 1996. That year he managed to win all the seven races at the Ascot racecourse in England and this made a lucky punter very rich. Darren Yates wagered £67.58 on the legendary jockey to win all his seven races at odds that exceeded 8000/1. For his courage and inspiration, he was rewarded with a huge paycheck of £550,823. This remains to this day one of the biggest payouts in horse racing.
FAQ: Your questions on the biggest winning bets answered
Billy Walters can brag about the biggest betting wins when he wagered $3.5 million on the New Orleans Saints. He was already a millionaire when they defeated the Indianapolis Colts but became much richer.
Walters is also the record holder for the biggest bet ever placed. There are not many punters who can brag about investing $3.5 million on a single match, especially when betting on the underdog.
Fred Craggs became a millionaire while investing only a fraction of a pound on horse racing. His bet at odds of more than 2 million to 1 is arguably the biggest in the history of bookmakers.
Some of the biggest winning betting football bets were placed by anonymous punters. The gambler from Malta who wagered £.80 to win £585,000 is the record holder for the biggest football bet ever won.
The official figures are not public for the biggest win ever, but punters can claim up to €2 million per bet. It is only fair to assume that a high roller was at one point lucky enough as to win this much money.
Get inspired by the biggest winning bets of all time
We have reached the conclusion of our article talking about the biggest winning bets ever paid to punters. It was an inspiring ride and we hope that you were just as impressed with the accomplishments of fellow punters. These success stories are not singular and over the years there were many more punters who were capable of turning small bets into fortunes. Whether you bet on single games or accumulators, with the right information, proper research and a lot of luck, you can join the list of sports betting millionaires.
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