The 25 Biggest and Most Monumental Sports Betting Wins Ever

In this guide we will be listing some of the biggest sports betting wins ever claimed by punters around the world. Get ready to feel inspired!

List of All-Time Biggest Sports Betting Wins

Looking for some of the biggest betting wins for inspiration as you place your next bet? Here’s a list of some of the biggest sports betting wins of all time:

25. Adrian Hayward – £25,000 on a £200 bet

In 2005, Liverpool fan Adrian Hayward bet £200 on midfielder Xabi Alonso to score from his own half at odds of 125-1. Alonso did not disappoint, and in 2006, when Liverpool played against Luton Town in the FA Cup’s third round, he scored a goal on the opposite end of the field in the closing minutes. The goal resulted in Liverpool’s 5-3 win, and Adrian Hayward gained a whopping £25,000, one of the biggest football betting wins ever. 

“I've been a Liverpool supporter for 26 years and I noticed last season that Alonso attempted shooting from his own half quite a few times. I couldn't get it out of my head that he would eventually score like it,” Adrian excitedly revealed.

“Since placing the bet, I've always had a vision in my mind that it would come when the opposing keeper came out for a corner in a cup game. I couldn't believe it when Luton got a corner and the keeper started to run upfield….I thought I was going to pass out. When it went in, I went crazy.”

24. Anonymous punters – $76,000 on a $0.10 bet

Two unnamed punters in Saratoga Springs, USA, bet $0.10 on a superfecta, which refers to predicting the first four horses to come in and naming their exact order. As one can imagine, the odds are high – with the winner being an 88/1 outsider, making it an obvious choice for our biggest betting wins. Naturally, the punters’ $76,000 (around £58,000) win came as a surprise after having correctly forecast the outcome.

23. Tayla Polia – $105,000 on a $5 bet

Tayla Polia successfully won on 20,000-to-1 odds for a 15-leg parlay when betting on the NFL, with minimal previous betting experience. In fact, Tayla claims she had only placed one bet prior to her infamous win! Her picks were Vikings -5, Falcons +3, Texans +1, Chiefs -8, Redskins +1, Patriots -14, Cardinals -4, Giants +5, Seahawks -14, Packers -3, Chargers -2, Steelers -6, Steelers/ Broncos over 45, Bengals -4, and Lions +3. Her accurate bets won her an exciting $105,000 (around £80,000) with William Hill, one of the biggest football betting wins.

22. Gerry Mcllroy – £100,000 on a £200 bet

In 2004, Gerry Mcllroy confidently bet that his son and golfer Rory Mcllroy, then aged 15, would win the British Open within ten years at odds of 500-1. Gerry’s friends soon followed suit and also placed bets on Rory’s golfing skills, which led to a payout of £100,000 to Gerry and £80,000 to his friends. Rory’s success was achieved by two shots over Spain’s Sergio Garcia and the U.S.’ Rickie Fowler.

“Although we're facing heavy losses, we can't help but admire the foresight of Rory's dad and his pals a decade ago,” said Ladbrokes spokeswoman Jessica Bridge.

Not just one of the biggest sports betting wins, but one of the most interesting too.

21. Nicholas Newlife – £101,840 on a £1,520 bet

When one thinks of the biggest betting wins, Nicholas Newlife’s story never fails to come to mind. After watching Roger Federer in 2003 Wimbledon, Nicholas predicted and bet on his future successes – and sure enough, Federer’s seventh Wimbledon win took place almost a decade later. However, Newlife passed away in 2009 and never got to enjoy one of the biggest ever betting wins, which was instead donated towards poverty charity Oxfam, just like all of his belongings.

20. Peter Edwards – £125,000 on a £50 bet

Harry Wilson became a successful football player at the tender age of 16. Just 15 years prior, his grandfather, 62-year-old Peter Edwards, foresaw the unforeseeable and bet that his grandson would eventually represent Wales as a professional footballer. Wilson sure didn’t let his grandfather down, who retired happily upon his grandson’s win. One of the biggest betting wins, and one of the most inspiring.

19. Mick Gibbs – £157,000 on a £2.50 bet

Back in 1999, Mick Gibbs forecast nine football games across Europe and was awarded an incredible £157,000 upon winning the accumulator bet. Despite this figure being an impressive one, among the biggest betting wins, Gibbs’ future win would still manage to top it! Keep reading to find out more…

18. Richard Hopkins – £165,000 on several bets

When Richard Hopkins of Peterborough took his son Evan go-kart racing in 1998, he could not help but notice go-kart driver Lewis Hamilton’s impressive skills. He proceeded to place several bets on him, starting with a £200 bet on Hamilton winning a Grand Prix by the age of 23 at odds 300. He then placed a bet of £100 on Hamilton winning the World Championship by the age of 25 at odds 500, and an additional £50 on both the predictions to take place at odds 1,500. A decade later, Hamilton won his first Formula 1 World Championship and Hopkins earned an astounding £165,000.

17. Vegas Dave – $200,000 on a $20,000 bet

Dave Oancea, a renowned gambler from Las Vegas, enjoyed a record month in November 2015 due to being responsible for two of the biggest betting wins in sports gambling. One of the two took place at UFC 193, where Oancea successfully bet on Holly Holm beating Ronda Rousey on 11-1 odds and won $200,000 (just over £150,000).

16. Anonymous punter – $250,000 on a $8,500 bet

An unnamed MGM Resorts sports book bettor enjoyed one victorious NFL weekend in 2017 after hitting on five legs of an $8,500 parlay. The Detroit Lions accounted for the fifth leg, beating the New York Giants with a score of 24-10. With a final $250,000 (around £191,000) awarded, it is safe to say that this bettor must have felt triumphant having earned one of the biggest ever betting wins. 

15. Anonymous punter – £200,000 on a £100 bet

Leicester City winning the Premier League in 2015 is a story that won’t easily be forgotten. Backing a winner of a big tournament is regularly one of the most popular football betting markets. But there were few backing Leicester at the time. The 5000/1 underdogs shocked many with their victory, but one anonymous punter sure had his day made, obtaining one of the biggest football betting wins of all time at £200,000! This also happened to be a lucky bet for Leigh Herbert who had placed a mere £5 on the same odds while on holiday and won a hefty £20,600 thanks to the Foxes.

14. Anonymous punter – $305,375 on a $5 bet

2016 was a lucky year for one Las Vegas resident at William Hill sportsbook, which requires a $5 weekly entry free for participation. The bettor correctly selected 12 basketball winners on a parlay card throughout one weekend and chose two NBA winners, being the Detroit Pistons and the Golden State Warriors. The total figure amounted to $305,375 (around £233,000).

13. Erick Lindgren – $340,000 on a bet placed by other professional players

Erick Lindgren was not new to the world of professional poker, but this win certainly outdid his previous! A few professional players once bet that Lindgren would not manage to play four straight rounds of golf in one day in Las Vegas’ boiling climate while carrying his own clubs and shooting below a 100 in each round from the pro tees. They were mistaken, leading to one of biggest betting wins. Amazingly, Lindgren succeeded and won $340,000 (about £259,000).

12. Anonymous punter – $375,000 on a $500 bet

An anonymous bettor placed two bets at the MGM sports book in Las Vegas before the 2011 MLB season. He initially wagered $250 on the St. Louis Cardinals winning the National League pennant, and then bet an additional $250 on them winning the World Series later in the year. His hopes were satisfied when St. Louis did indeed win, and the bettor enjoyed a total of $375,000 (about £286, 000).

11. Phil Mickelson – $560,000 on a $20,000 bet

Professional golfer Phil Mickelson had high hopes for the Baltimore Ravens at the Super Bowl, even before the 2000 NFL season. After observing Baltimore’s 6-2 success in the previous season, Mickelson formed a betting syndicate and bet $20,000 at 22/1 odds, earning $560,000 (about £426,000) in return! What’s so amazing about this example of biggest sports betting wins is that it was a achieved without the use of an accumulator. 

10. Mick Gibbs – £500,000 on a £0.30 bet

Mick Gibbs, a roofer by profession, has found himself on our list of biggest betting wins for the second time! Just two years after his first big win, Gibbs chose to put down 30 pence on a 15-leg accumulator bet with astonishing odds of 1,666,666/1. Gibbs predicted the first 14 games correctly, with the final Champions League match between Bayern Munich and Valencia ending in penalties, and Bayern Munich’s goalkeeper making a move that won Gibbs a substantial figure!

9. Darren Yates' Magnificent Seven – £550,000 on a £62 bet

Darren Yates placed a fantastic bet in 1996 that would see him become a big name in horse racing. The great win, which is widely referred to as the ‘magnificent seven’, took place when Yates successfully wagered £62 on jockey Frankie Dettorri winning all seven of his rides on that day at Ascot.

8. Anonymous punter – £585,000 on an £0.80 bet

In November 2011, an anonymous punter from Malta bet 80 pence through William Hill on a 19-match accumulator with odds of 683,738/1. All predictions were correct and ended with Liverpool scoring a winning goal in the last few minutes before closing, beating Chelsea and earning this punter one of the biggest ever betting wins. .

7. Charles Barkley – $800,000 on a $500,000 bet

NBA Champion Charles Barkley boasts an easily remembered name in sports betting. He was not new to big wins, but the greatest of all took place when he wagered on the New England Patriots winning the Super Bowl – which was thought to be unlikely at that time, given that they were a 14-point underdog against the St. Louis Rams in 2002. Upon their win, which would be Tom Brady’s first of many, Barkley gained a monumental $800,000 (about £608,000).

6. James Adducci – $1.2 million on an $85,000 bet

James Adducci’s bet on Tiger Woods is one that will go down in history as a bold, yet highly rewarding move. Woods’ 2019 Masters Victory was his first key championship win in 11 years, and choosing to bet $85,000 on a golfer who had not won a championship in that long sounds incredibly risky to most of us! Adducci certainly knew what he was doing, though – as his brave initiative paid off, bringing in $1.2 million (about £760,000) and breaking William Hill’s record for the largest ever individual payout on a futures bet, as well as being one of the biggest betting wins in general. 

You should also check the Cheltenham betting odds and see if it works for you.

5. Mike Futter – £800,000 on betting his own horse

Mike Futter’s name isn’t unheard of in the betting industry – but this one major win increased his recognition tenfold. In 2003, Futter gambled his own horse: Monty’s Pass. The horse did not let him down, and Fetter was awarded £348,000 for being Monty’s Pass owner, and then over an additional £400,000 for successfully betting on his horse from 40/1 down to 16/1 odds.

“I've had some fantastic bets and fantastic days but this is one I will never forget,” said a delighted Futter.

4. Fred Craggs – £1 million on a £0.50 bet

Fred Craggs, a 60-year-old fertiliser salesman from Yorkshire, one day placed a bet that would change his life and allow him to be remembered as one of the most renowned names in sports betting. Craggs wagered a mere 50 pence on an eight-fold accumulator, making smart choices on horse races around the globe, and received a whopping seven-figure amount in return. Funnily enough, Craggs wasn’t even aware of his win until returning to the bookmaker for another hand at gambling – and he would have earned a total of £1.4 million, if only he had chosen a no-limit bet. Still not too bad of a prize, right?

3. Steve Whiteley – £1.5 million on a £2 bet

Steve Whiteley, a 61-year-old heating engineer, enjoyed a truly successful bet in 2011, when he made use of a free ticket to enjoy the horse races and placed a £2 bet. Certainly one of the cheapest stakes on our list of biggest betting wins. Whiteley correctly chose the six horses on that day, one of which had lost in all of its 28 races in the past, and benefited from £1.5 million.

2. Vegas Dave – $2.5 million on a $140,000 bet

Do you remember when we wrote of Dave Oancea and his record-breaking 2015? His second successful win happened one week into the 2015 MLB season, when Oancea bet on the Kansas City Royals to win the World Series at 30/1 odds. His $140,000 bet required quite the effort, after having to be split across 15 different casinos as they wouldn’t take on his liability. In fact, many presumed him crazy for the risk he was about to take but it ultimately paid off, with the Kansas City Royals defeating the New York Mets. Oancea enjoyed a $2.5 million prize (about £1.9 million).

1. Billy Walters – a successful $3.5 million bet

We’re concluding our list with Billy Walters and his massive win seen in 2010, when the New Orleans Saints played against the Indianapolis Colts at the Super Bowl XLIV. Walters began his journey in gambling through playing poker, prior to taking on sports betting. He has successfully earned gigantic figures and is known for his  record-breaking winning streak, which verifies that sports betting is not simply for the fortunate, but does indeed require skill. After some careful consideration, Walter placed a successful $3.5 million (about £2.7 million) bet on the New Orleans Saints, who were also the underdogs. They won their first ever Super Bowl against the Colts by 31-17. Not just one of the biggest sports betting wins, but one of the biggest ever betting wins period. 

GB

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Biggest Betting Wins Of All Time

Sports betting has come a long way – from the days when horse races were reserved for those of an upper social class, to the unending list of online bookies found nowadays. In fact, the first online betting platforms only originated towards the end of the 90s – and look at the many options now! One can only imagine what the world of sports betting has yet to introduce…

It certainly has increased in popularity over recent years – and why wouldn’t it? Not only is sports betting an incredibly exciting hobby to take up, but the chances of earning a substantial amount of money make it all the more enjoyable! Moreover, sports betting is often regarded as one of the most accessible types of betting, as anyone willing to expand on their passion for sports may give it a go. You can bet stakes as low as a few pence to much higher numbers. A punter once placed around £1,000,000 on Floyd Mayweather to beat Connor McGregor in 2017!

Which Are The Bookies With The Biggest Betting Wins?

In terms of telling you which bookmakers consistently provide the biggest betting wins; the truth is that information is simply not available. We can only give bookmaker specific examples which have been picked up by the press as most remain unreported and anonymous. However, there are some examples, as you have seen from the likes of William Hill and others in our above list. Some other examples include:

What Do The Biggest Betting Win Examples Mean For Me?

In terms of who has the potential to offer the biggest betting wins for you, historical examples don’t matter all that much. What is relevant is twofold. Firstly, that they have a high enough payout limit and secondly, are trustworthy with their payouts.

Just because an operator doesn’t appear on our list, for instance, doesn’t mean they don’t have the potential to offer the biggest betting wins. During our research for the biggest payouts nothing really came up for bet365s biggest wins. This isn’t too unusual, most big wins don’t make the paper unless they have an especially interesting hook to keep readers interested. But we do know that bet365 have both extremely high deposit limits and one of the best reputations for security and fairness of any betting site.

This means that even though they don’t appear on our list with bet365 biggest wins in the same way William Hill do, we would view both equally excellent options for the biggest betting wins. There is no absolute and comprehensive list of bookies with the biggest ever betting wins, because most are private, instead our list of top bookmakers is largely based on maximum payout, alongside trustworthiness.

There are other factors we considered too, for instance many betting sites will have a maximum bet amount based on the liquidity of the market – being generous in this regard was also important in getting a place on our list.

Which are the bookies with the biggest ever betting wins? We don’t entirely know; we only have access to those publicised. But we can say that our list provides what sites have the potential for providing the biggest betting wins heading into the future.

Payment Methods With The Biggest Betting Wins

So, we now know that the bookies with the biggest betting wins, or at least the potential to provide such big sports betting wins, are tied to a couple of key factors with none of them being more important than maximum payout. And we’ve provided a list based on maximum payouts for that exact reason.

However, there’s an additional consideration because our list of maximum payouts takes the most you can get out of any payment method. It does not account for specific payment method limits and some bookmakers have different maximum payouts for different payment methods.

Typically, if there is a distinction made, your most popular payment options such a debit card, would have the highest limits, while things like e-wallets and prepaid cards might be lower. It’s also important to note that payment methods are also often distinguished by maximum deposits too.

The Impact Of Promotions On Maximum Payouts

Sometimes, a promotion will cap the maximum payouts which can be won while using that bonus.

A typical example of this would be with a no deposit betting offer, to prevent exploitation of the generosity of the operator. So, for instance, you may get £5 to bet on any sport, but winnings from that bet to be capped at £200. Other free bets, which do require a deposit, may also receive similar treatment. The only way to know for sure is to check your promotional terms and conditions.

Maximum Casino Payouts

While our focus here is of course on the biggest sports betting wins and payouts, we know that many of our readers are interested in both sportsbook and the best casino sites the UK has to offer.

And, if they are reading this article about biggest ever betting wins, they are probably interested in how the world of casinos fits into all of this.

Well, they can be a little different because casino payout limits actually tend to be based more on the individual game, especially when we are talking about the best betting slots, rather than a general rule across the site. A casino game will often have an advertised maximum jackpot, and that would create your biggest betting wins and payouts. In the case of the finest poker sites, it comes down to what is played and the limits of the table. As that is more of a peer-to-peer experience, with the operator providing a platform for play.

Things To Keep In Mind When Aiming For Big Betting Wins

Those big betting sports wins are always entertaining to learn about.

Not only can they often be amazing stories, but they show us that it’s possible for a normal person, through their own sheer luck and/or sports prediction prowess, to achieve something truly incredible.

However, being inspired doesn’t, unfortunately, mean we can all enjoy being recipients of the biggest betting wins. That said, if you are aiming big, there’s a few things that you can keep in mind to improve your chances.

Biggest Accumulator Betting Wins

There are essentially three ways the biggest betting sporting wins come to be.

The first possibility is that the stake to begin with was enormous, and thus any winnings would also, with any kind of reasonable betting odds, also be similarly massive.

The other possibility is that an amount was bet on an enormously unlikely (or so it seems at the time) single event, such as Leicester City winning the Premier League.

Most often though, as you will see from the many examples given in this article, come from accumulators, which means that they are the result of many bets all being successful to create such enormous odds and payouts.

This also means many of the biggest betting wins were through small amounts, and will be for many of our readers, the safest, most interesting, and best opportunity for biggest betting wins. Even better, many operators offer great promotions for lengthy accumulators, providing even bigger winnings. Here’s a final few monster acca examples to showcase exactly what we mean.

ThePuntersPage Final Say

It's clear that the biggest betting wins come in many shapes and sizes. They can be as a result of many different sports, different kinds of bets and even from a broad spectrum of often fascinating individual stories that accompany them. They aren’t just interesting to learn about but also give us an important way of testing the upper limits of our best bookmakers. They also provide inspiration for bets of all sizes.

And while you can certainly improve your chances of winning big by utilising sound logic, strategy and betting tips, it’s important to remember that these huge wins do come with appropriately large odds.

That doesn’t mean you shouldn’t shoot for the stars with that monster accumulator or back your favourite underdog to win the big one, all of that is a vital, thrilling part of online betting. However, we would say that every win, no matter the size is monumental. Even more so if you had fun. In fact, if we make enjoyment our betting priority, we can all be winners.

Written by Natalya Vukovic View all posts by Natalya

Natalya is a writer and content creator with experience writing across the sports betting and financial sectors. When not writing, Natalya can be found illustrating or snapping a multitude of photographs.

natalya@thepunterspage.com

Viewed and Reviewed by Kevin Dolan

Kevin Dolan is an Irish professional sports bettor currently operating with Wagertalk Inc, the world's largest sports betting service and in 2015 became the first foreigner ever to win the prestigious World Series of Handicapping contest in Las Vegas, Nevada.

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