Biggest Betting Wins In The History

There are quite a few success stories out there about people who tried their luck and got their money’s worth and more.

While the odds are rarely ever in your favour when you’re placing bets, the stars can align at times and help you take home massive winnings. The following examples show just how well taking risks can pay off.

Top 10 biggest betting wins (editors’ picks)

Nicholas Newlife won £101,840 after his death.
Dave Oancea holds two of the biggest sports betting wins.
Sean Connery’s single game of roulette won him £163,000.
A 25-year-old won $39.7 million in a casual game of video slots with a $100 deposit.
84-year-old Gloria McKenzie has the highest single winning record in Powerball, winning $590.5 million.
An anonymous punter from Malta won £585,000 on a £0.80 bet, beating the odds of 683,738/1.
Betting on Tiger Woods in 2019, James Adducci found himself $1.2 million richer.
Placing a single bet on 17 in roulette, Mike Ashley immediately won $1.6 million.
The biggest online gambling win to date belongs to a Mega Moolah Jackpot player who got €18.9 million.
After a single spin on Megabucks, Johanna Heundl hit the $22.6 million jackpot.

Full list of all-time biggest betting wins

Not everyone can go home with the biggest sports betting win in history or earn millions of dollars after a single night at a casino. The odds of that happening are incredibly slim, but there’s always a chance! You never know when lady luck might cast her glance on you, and that’s precisely why so many people are drawn to gambling.

With millions of people around the world testing their luck daily, someone’s always bound to hit it big.

Whether it’s hitting the jackpot, lucking out at the roulette table, or placing the perfect bet on betting sites, take a look at a few of the biggest betting wins in the UK and abroad in the past few decades.

1. Adrian Hayward - wins £25,000

Xabi Alonso helps Adrian Hayward take home £25,000

Name: Adrian Hayward
Amount won: £25,000
Bet amount: £200
Type of bet: Sports betting
Game: Liverpool vs Luton Town (football)‍
Odds: 125 to 1

Sports betting is quite unique. If you want to win, you cannot rely solely on luck – you have to analyze the players, assess their skills, know your odds of winning, and make fact-based predictions on their future performance. And that’s exactly what Adrian Hayward did when placing his £200 bet on Liverpool’s midfielder Xabi Alonso.

A Liverpool fan and supporter for over 26 years, Adrian noticed in 2005 that Xabi had been trying to score from his own half several times. Convinced that the Xabi’s attempts would eventually pay off, Adrian placed his bet, despite the odds being 125/1 against him.

In 2006 during the Liverpool vs Luton Town game in the FA Cup’s third round, finally Xabi Alonso scored a goal from his own half within the final minutes, resulting in Liverpool’s win and earning Adrian Hayward no less than £25,000.

2. Anonymous bettor - wins $76,000

$0.10 bet pays off for two anonymous punters

Name: Anonymous
Amount won: $76,000
Bet amount: $0.10
Type of bet: Sports betting
Game: Superfecta (horse racing)‍
Odds: 88 to 1

Who would’ve thought that a tiny little $0.10 bet could turn into thousands of dollars worth of winnings? Certainly not the two anonymous punters from Saratoga Springs who made it happen and got to go home with $76,000.

The punters placed a high-risk bet on horse racing known as a superfecta. For the uninitiated, a superfecta is a type of wager where you’re to predict the first four horses that’ll finish the race in the exact order that they come in. Unsurprisingly, the odds of making such an accurate prediction are minuscule, about 88/1. Still, the Saratoga Springs residents beat the odds, much to their surprise, after correctly predicting the order of the first four horses to finish the race.

3. Tayla Polia - wins $100,005

Beating 20,000 to 1 odds comes easy to Tayla Polia

Name: Tayla Polia
Amount won: $100,005
Bet amount: $5
Type of bet: Sports betting
Game: 15-leg NFL parlay (American football)‍
Odds: 20,000 to 1

One of the biggest long shots in betting history goes to Tayla Polia, who successfully beat 20,000 to 1 odds and won $100,005 in 2015. The 26-year-old placed an astonishing 15-leg NFL parlay with a $5 deposit and earned her winnings by choosing the right point spread in 14 games.

To make the story even more fascinating, this was only the second time Tayla had placed a bet in her entire life. According to her, she decided to place the bet after spending her Sunday morning discussing spreads with her boyfriend. Apparently, she couldn’t understand how the system worked, so she just followed her gut feeling when placing the parlay. Sometimes, it’s all just a matter of luck.

4. Gerry Mcllroy - wins £100,000

Belief in his son wins Gerry Mcllroy £100,000

Name: Gerry Mcllroy
Amount won: £100,000
Bet amount: £200
Type of bet: Sports betting‍
Game: British Open (golf)

In this wholesome story, Gerry Mcllroy won £100,000 (approximately $183,000) after making a moneyline bet of £200 on his son winning the British Open within a decade. At the time, his son was only 15 years old, but Gerry had complete faith in him and displayed his immense power of foresight.

Within a few years, his son, none other than the golfer Rory Mcllroy, beat Spain’s Sergio Garsia and the US’s Rickie Fowler by two shots to secure a win at the British Open.

Gerry ended up winning £100,000, and his friends who had the same faith in Rory won £80,000.

5. Nicholas Newlife - wins £101,840

Nicholas Newlife wins a life-changing £101,840

Name: Nicholas Newlife
Amount won: £101,840
Type of bet: Sports betting‍
Game: Tennis

Nicholas Newlife would be proud to have one of the biggest sports betting wins in history. Back in 2003, Newlife was amazed at Roger Federer’s (one of the highest paid athletes) skills during Wimbledon, so much so that he placed a bet on the tennis player’s future success.

Almost ten years later, the bet would pay off as Federer won his seventh Wimbledon game. Unfortunately, though, Nicholas Newlife passed away before he could collect his £101,840 (approximately $186,000) in winnings. The prize, as well as all of Newlife’s belongings, went to Oxfam International – a charitable organization fighting against global poverty.

6. Peter Edwardson - wins £125,000

Peter Edwardson glimpses into the future and earns £125,000

Name: Peter Edwardson
Amount won: £125,000
Bet amount: £50‍
‍Game: Football

Every grandparent dreams of seeing their grandchildren succeed and make a name for themselves, and Peter Edwardson was no different. He dreamed of his 1-year-old grandson becoming a professional football player one day and representing Wales, and he even placed a £50 bet on it.

As fate would have it, the bet paid off when his grandson Harry Wilson became a successful footballer at the young age of 16. Edwardson collected his £125,000 winnings and retired. Whether it was a self-fulfilling prophecy or a stroke of good luck, we’ll never know.

7. Dave Oancea - wins $200,000

Dave Oancea starts his November with an extra $200,000

Name: Dave Oancea
Amount won: $200,000
Type of bet: Sports betting
Game: UFC‍
Odds: 11 to 1

November of 2015 was an astonishingly lucky month for Dave Oancea, nicknamed Vegas Dave. He got not one, but two of the biggest sports betting wins in a matter of weeks. The first of the two victories was at UFC 193.

Oancea decided to go against the odds (of 11/1) and wagered that Holly Holm would beat Ronda Rousey, and wouldn’t you know it, that’s precisely what happened. Dave happily collected his $200,000 (approximately £150,000) and went on to have an even better November later on (which we’ll discuss in a moment).

8. Sean Connery - wins £163,000

Sean Connery stays true to his James Bond character and takes home £163,000

Name: Sean Connery
Amount won: £163,000
Type of bet: Casino
Game: Roulette‍
Odds: 50,000 to 1

Not even James Bond himself would be able to do what Sean Connery did at an Italian casino in the Alps. Casually walking up to the roulette wheel, Mr. Connery placed his money on the number 17, but had no luck with his first two tries. Still committed to his seemingly favorite number, real-life James Bond stuck to 17 and won on the third roll.

He didn’t stop there. He left his winnings on 17, and wouldn’t you know it – 17 rolled again. Not satisfied just yet, Sean Connery left all his winnings on 17 once more, and 17 rolled up for the third time in a row, beating the incredible odds of 50,000/1. He collected 17 million lire (approximately £10,000) which would be about £163,000 in today’s market. It was an incredible feat, even for a James Bond character.

9. Anonymous bettor - wins $250,000

Anonymous bettor finishes the NFL weekend with +$250,000 in their account‍

Name: Anonymous
Amount won: $250,000
Bet amount: $8,500
Type of bet: NFL parlay‍
Game: Detroit Lions - New York Giants (American football)

Hitting five legs on a parlay isn’t a common occurrence, but one bettor made it happen. The anonymous bettor at MGM Resorts placed an $8,500 parlay, betting on the Detroit Lions to beat the New York Giants in the fifth leg. With a score of 24-10 for the Detroit Lions, the bettor finished the NFL weekend in 2017 triumphantly and collected $250,000 (approximately £191,000).

10. Mick Gibbs - wins £157,000

First of Mick Gibbs’ biggest betting wins makes him £157,000 richer

Name: Mick Gibbs
Amount won: £157,000
Bet amount: £2.50
Type of bet: Sports betting‍
Game: Football

We can’t talk about the biggest betting wins in the UK without mentioning Mick Gibbs. Before the turn of the century, Gibbs placed a £2.50 football bet, forecasting the results of no less than nine football games around Europe. The accumulator bet made him £157,000 richer, and while these winnings were incredible by themselves, Gibbs’ good fortune hadn’t left him yet. His next win somehow topped that measly £157,000, and we’ll discuss that as well.

11. Richard Hopkins - wins £165,000

Lewis Hamilton’s fan Richard Hopkins accumulates £165,000 winnings

Name: Richard Hopkins
Amount won: £165,000
Bet amount: £350
Type of bet: Sports betting
Game: Formula 1‍
Odds: 1,500 to 1

Spending some quality time with your children pays off in more ways than one. Back in 1998, Richard Hopkins and his son went go-kart racing just for fun, and Richard couldn’t help but notice Lewis Hamilton driving around the course. Richard was so impressed with Hamilton’s skills that he went on to spend several hundred pounds betting on him.

In his initial bet of £200, Richard put his money on Hamilton winning the Grand Prix by the time he was 23. Soon after, he placed another bet, risking £100 that Hamilton would win the World Champion by 25. He was so sure of Lewis’s abilities that Richard placed an additional £50 on both of his previous bets, giving him odds of 1,500/1.

It took almost a decade, but Richard ended triumphantly with £165,000 in his wallet when Lewis Hamilton won the Formula 1 World Championship.

12. Anonymous bettor - wins £200,000

Anonymous bettor beats 5,000/1 odds and wins £200,000

Name: Anonymous bettor
Amount won: £200,000
Bet amount: £100
Type of bet: Sport betting
Game: Football‍
Odds: 5,000 to 1

Even the biggest Leicester City fans didn’t have much confidence in the team winning the Premier League back in 2015. However, one devoted supporter didn’t mind taking on the 5,000/1 odds and placing a £100 bet on their victory. Lo and behold, Leicester City shockingly took the victory and left the anonymous punter with £200,000 more in their bank account.

13. Anonymous bettor - wins $305,375

A $5 bet wins an anonymous punter $305,375

Name: Anonymous
Amount won: $305,375
Bet amount: $5
Type of bet: Sports betting‍
Game: Basketball

There’s no better feeling than getting a massive return on your investment, and one Las Vegas resident knows that for sure. The anonymous bettor only paid the $5 participation fee at one of the top betting sites William Hill sportsbook but successfully took home $305,375 after correctly selecting 12 winners in one weekend. Among the bettor’s choices were the Detroit Pistons and Golden State Warriors, two NBA winners.

14. Erick Lindgren - wins $340,000

Erick Lindgren takes on Las Vegas boiling climate and wins $340,000

Name: Erick Lindgren
Amount won: $340,000
Type of bet: Sports betting ‍
Game: Golf

This was an unorthodox win for Erick Lindgren, a professional poker player. Instead of winning in a game of poker, as would be expected, he won $340,000 (approximately £259,000) in a game of golf.

A few of the players bet that Erick would never be able to play four straight lines of golf in a single day while carrying his own clubs, shooting below 100, and taking on the extreme Las Vegas summer heat. Lindgren proved them wrong and collected his $340,000 by the end of the day.

15. Anonymous bettor - wins $375,000

A St. Louis Cardinals fan gets $375,000

Name: Anonymous
Amount won: $375,000
Bet amount: $500
Type of bet: Sports betting‍
Game: MLB (baseball)

Not many St. Louis Cardinals fans would have placed $500 on them before the 2011 MLB season, but that’s exactly what this anonymous bettor did. He first placed a $250 wager on the St. Louis Cardinals winning the National League. Then, he placed another $250 wager on the team coming out victorious in the World Series. Eventually, the St. Louis Cardinals came out on top, and the bettor received accumulated winnings of $375,000 (approximately £286, 000).

16. Charles Wells - wins 1 million Francs (over $500,000 today)

Charles Wells wins every chip on the table and takes home 1 million Francs

Name: Charles Wells
Amount won: $500,000
Bet amount: £400
Type of bet: Casino‍
Game: Roulette

Charles Wells wasn’t necessarily a great role model, but his story is truly one for the books. Back in 1891, Wells broke the bank at Monte Carlo and collected a million Francs (over $500,000 in today’s market) after an 11-hour marathon of roulette.

It all started when he ripped off £400 from his investors, claiming that he was inventing a musical jump rope. Instead, he set off for Monte Carlo and tried his luck at roulette. Amazingly, the stunt paid off, but his luck would quickly run out.

He ended up losing all of his winnings right there in Monte Carlo. Soon after, he got arrested in England for one of his notorious schemes. After serving eight years for fraud, and getting arrested a couple more times afterward, Charles Wells died without a penny to his name.

17. Phil Mickelson - wins $560,000

Golfer Phil Mickelson bets on Baltimore Ravens and wins $560,000

Name: Phil Mickelson
Amount won: $560,000
Bet amount: $20,000
Type of bet: Sports betting‍
Game: NFL (American football)

Phil Mickelson, a professional golfer, became quite a fan of the Baltimore Ravens even before they made it big in 2000. Seeing the team’s strength and talent after a good season, Phil made a betting syndicate and placed a $20,000 bet against the odds. It didn’t take him long to win his money back and then some, as he got to take home $560,000 (around £426,000).

18. Mick Gibbs - wins £500,000 (about $700,000)

Another victory for Mick Gibbs, who takes home £500,000 this time

Name: Mick Gibbs
Amount won: £500,000
Bet amount: £0.30
Type of bet: Sports betting
Game: Football‍
Odds: 1,666,666 to 1

Only a few short years after winning the accumulator bet of £157,000, Mick Gibbs tested his luck once again and wasn’t disappointed. He took on the odds of 1,666,666/1 and placed a mere £0.30 on a 15-leg parlay on the Champions League games. Gibbs predicted 14 games correctly and won an astonishing figure of £500,000, proving that lightning can indeed strike twice.

19. Charles Barkley - wins $800,000

In one of the biggest sports betting wins, $800,000 goes to Charles Barkley

Name: Charles Barkley
Amount won: $800,000
Bet amount: $300,000
Type of bet: Sports betting‍
Game: NFL (American football)

Every sports bettor knows who Charles Barkley is – an NBA superstar who’s helped many punters take home their winnings. But this time, it was Charles himself who took home the win. In 2002, he placed a $300,000 bet on the underdogs in the Super Bowl, wagering on the New England Patriots. The game marked Tom Brady’s first win, and Charles got $800,000 (about £608,000) in return.

20. Farren Yeats - wins £550,000

Farren Yeats’ “magnificent seven” wins him £550,000

Name: Farren Yeats
Amount won: £550,000
Bet amount: £62
Type of bet: Sports betting‍
Game: Horse racing

They say you shouldn’t place all your eggs in one basket, but it’s paid off for Farren Yeats. In 1996, he placed a £62 bet on Frankie Dettori to win all seven of his races for the day. In an astonishing victory, now known as the magnificent seven, Frankie Dettori surprised everyone, and Farren Yeats got a pay-off of £550,000.

21. Anonymous bettor - wins £585,000

An £0.80 bet gets a bettor £585,000

Name: Anonymous
Amount won: £585,000
Bet amount: £0.80
Type of bet: Sports betting
Game: Liverpool - Chelsea (football)‍
Odds: 683,738 to 1

In one of the most impressive sports betting wins, an anonymous bettor from Malta accurately placed a 19-leg parlay! Although their odds were 683,738/1, all of their predictions were on point, and when Liverpool scored the winning goal against Chelsea in the final minutes of the game in 2011, this bettor got to take home £585,000!

22. Mike Futter - wins £800,000 (about $1.1 million)

Mike Futter’s Monty’s Pass earns him £800,000

Name: Mike Futter
Amount won: £800,000
Type of bet: Sports betting‍
Game: Horse racing

One of the best bets in Mike Futter’s betting career was when he decided to wager on his own horse – Monty’s Pass. When Monty’s Pass won the race, Futter received £348,000 as his owner and an extra £400,000 for his successful bet.

23. James Adducci - wins $1.2 million

The largest-ever individual payout on a futures bet goes to James Adducci with $1.2 million

Name: James Adducci
Amount won: $1.2 million
Bet amount: $85,000
Type of bet: Sports betting‍
Game: Golf

Although Tiger Woods is one of the most famous professional golfers in the world, betting on him hasn’t always seemed like the smartest choice. This was especially true in 2019 when 11 years had passed since his last championship victory.

However, James Adducci had faith in Woods and placed $85,000 on him despite the low odds. When Tiger Woods won the Masters Tournament, Adducci got a huge pay-off of $1.2 million. The history of betting has been made, making it the biggest individual payout on a futures bet.

24. Fred Craggs - wins £1 million (about 1.4 million)

One of the biggest sports betting wins sees Fred Craggs £1 million richer

Name: Fred Craggs
Amount won: £1 million
Bet amount: £0.50
Type of bet: Sports betting
Game: Horse racing‍
Odds: 2,800,000 to 1

Fred Craggs became one of the most famous sports bettors seemingly overnight. He placed a small £0.50 bet on an eight-leg parlay with odds being 2,800,000/1. He chose his horses very carefully but didn’t believe much would come out of it. He earned an astonishing £1 million that changed his life.

Funnily enough, Craggs didn’t even know he won until he went back to his bookmaker to place a new, unrelated bet.

Had he chosen a no-limit bet, his earnings would be £1.4 million but £1 million rolls off the tongue more easily anyways.

25. Mike Ashley - wins $1.6 million

Billionaire Mike Ashley instantaneously wins $1.6 million playing roulette

Name: Mike Ashley
Amount won: $1.6 million
Type of bet: Casino‍
Game: Roulette

Although some of the biggest betting wins in the UK do create heartwarming from-rags-to-riches stories, that’s not always the case. Still, that doesn’t make billionaire Mike Ashley’s story any less fascinating.

Back in 2008, the owner of the Newcastle United Football Club stopped by the Fifty casino for just one game of roulette. He bet once on the number 17 and instantaneously won $1.6 million. Ashley collected his winnings, and that was the end of it all. Perhaps Sean Connery and Mike Ashley are onto something with 17?

26. Steve Whiteley - wins £1.5 million

A free ticket to horse racing gets Steve Whiteley £1.5 million ‍

Name: Steve Whiteley
Amount won: £1.5 million
Bet amount: £2
Type of bet: Sports betting‍
Game: Horse racing

Back in 2011, Steve Whiteley received a free ticket to the horse races, so he went to enjoy his day. He placed a £2 bet on the six winners for the day, and surprisingly he got them all right. Whiteley even chose one of the horses that had lost all 28 of its past races, but luck was on his side that day. Steve Whiteley won £1.5 million, earning him a spot on the list of the biggest betting wins in history.

27. Dave Oancea - wins $2.5 million

Dave Oancea on a roll in 2015, winning an extra $2.5 million ‍

Name: Dave Oancea
Amount won: $2.5 million
Bet amount: $140,000
Type of bet: Sports betting‍
Game: Kansas City Royals - New York Mets (MLB baseball)

We’re still not through Dave Oancea’s impressive November of 2015. As mentioned, his first betting victory made him $200,000 richer, but that’s nothing compared to his second one. Vegas Dave took his winnings and went on to place a $140,000 bet on the Kansas City Royals’ victory in the World Series. Just placing the bet was difficult enough as no single casino was willing to take on his liability. So, he had to split the bet across 15 casinos.

Everyone thought he went insane until the Kansas City Royals beat the New York Mets and Dave Oancea received $2.5 million in return!

28. Billy Walters - wins $3.5 million

New Orleans Saints win Billy Walters $3.5 million

Name: Billy Walters
Amount won: $3.5 million
Type of bet: Sports betting‍
Game: New Orleans Saints - Indianapolis Colts (NFL American football)

Billy Walters started his gambling career in poker but quickly turned to sports betting. In a short time, he became known for his insane wins and amazing streaks, proving that betting isn’t just a matter of luck but of skill as well.

One of his biggest sports betting wins left him with an extra $3.5 million in his bank account. During the Super Bowl in 2010, he bet on the New Orleans Saints, the underdogs, beating the Indianapolis Colts. It was their first-ever victory against the Colts in the Super Bowl.

29. Beverly Whitten - wins $3.7 million

A retired teacher, Beverly Whitten hits the jackpot and wins $3.7 million‍

Name: Beverly Whitten
Amount won: $3.7 million
Type of bet: Casino‍
Game: Slot machine

To celebrate her retirement, now a former teacher Beverly Whitten decided to treat herself by testing her luck at the slots. She didn’t expect much, just a few hours of enjoyment. But, after two hours at the “Golden Chamber”, Beverly was shocked to see that she hit the jackpot of $3.7 million! Not knowing what to do with all of that cash, she made a deal with the casino to receive her prize in installments of $1,945 a month.

30. Amy Nishimura - wins $8.9 million

Lady Luck casts her glance on Amy Nishimura and wins her $8.9 million

Name: Amy Nishimura
Amount won: $8.9 million
Bet amount: $100
Type of bet: Casino‍
Game: Slot machine

If you want something, all you have to do is ask – at least that’s the philosophy of 71-year-old Amy Nishimura. She visited Vegas for the holidays, and before long, she ended up with under $100 in her wallet. Approaching a slot machine that “spoke” to her, she explained her dire situation to the machine and asked for good luck.

After three hours of playing, Amy’s prayers were answered, and she hit the $8.9 million jackpot.

31. John Tippin - wins $11 million

John Tippin gets a life-changing $11 million win

Name: John Tippin
Amount won: $11 million
Type of bet: Lottery‍
Game: Megabucks playslip

John Tippin, a simple postal worker, was just another Vegas visitor in 1996 who wanted to have some fun and test his luck with a small Megabucks playslip. And luck was definitely on his side when he won a life-changing $11 million!

However, it’s not all rainbows and butterflies when you find yourself with so much money overnight. In 2001, John Tippin published his book “I Did It: My Life After Megabucks” where he explains the paranoia and isolation that accompanied such huge winnings.

32. Peter - wins €11.7 million

Online gambling paid off for Peter who took in €11.7 million

Name: Peter
Amount won: €11.7 million
Type of bet: Casino‍
Game: Progressive jackpot slots

Online gamblers have as much of a chance of supercharging their savings as any Vegas visitor. Peter, a Norwegian online gambler, learned that first-hand when he won €11.7 million in a game of progressive jackpot slots at Betsson online casino.

33. Don Johnson - wins $15 million

Don Johnson negotiates his way to $15 million

Name: Don Johnson
Amount won: $15 million
Bet amount: $25,000 a hand
Type of bet: Casino‍
Game: Blackjack

Don Johnson is one-of-a-kind. While he does have a few great strategies for success in blackjack, most of his winnings are thanks to his unparalleled negotiation skills.

Although some casinos offer a guaranteed 10% payback to high-rollers like Mr. Johnson, he negotiated his way to a 20% payback for bets up to $25,000 a hand. Within six months, he collected over $15 million from three casinos playing like that.

34. Archie Karas - wins $17 million

With ups and downs, Archie Karas finds himself with $17 million

Name: Archie Karas
Amount won: $17 million
Bet amount: $10,000
Type of bet: Casino‍
Game: Razz (poker)

Archie Karas’ success story was a true rollercoaster with enough ups and downs to make you feel lightheaded. His story starts with a small bet of just $50. Initially, he lost $2 million in a poker game in LA, then went to the Binion’s Horseshoe in Vegas to try and win something back in high stakes Razz. Spotting a friend, he borrowed $10,000 and soon enough found himself with $17 million in winnings, paying back the friend with 50% interest.

Between 1992 and 1995, Archie continued gambling, winning and losing millions at a time, and it’s estimated that his bankroll exceeded $40 million at one point. However, he ended up losing all of his money playing craps, poker, and baccarat. Eventually, Karas got banned from all Las Vegas and Nevada casinos for life.

35. Elmer Sherwin - wins $21 million

Elmer Sherwin hits two jackpots and goes home with $21 million

Name: Elmer Sherwin
Amount won: $21 million
Type of bet: Casino
Game: Slot machine‍
Odds: 50 million to 1

A World War II veteran, Elmer Sherwin didn’t win just one but two multi million jackpots in his gambling career in 1989, just a few hours after the Mirage’s opening. He won $4.6 million and over the next few years he continued testing his luck at casinos around the world.

After 16 years, his persistence certainly paid off. At the ripe old age of 92, Elmer hit the $21.14 million jackpot, beating the odds of 50 million/1.

36. John Heywood - wins €17.8 million (about $21.2 million)

John Heywood breaks records with a €17.8 million Mega Moolah win ‍

Name: John Heywood
Amount won: €17.8 million
Type of bet: Online betting‍
Game: Mega Moolah slot machine

Whether online or offline, most gamblers spend years testing their luck and learning to appreciate the small victories along the way. However, it only took John Heywood less than 25 minutes to take the win that most gamblers can only dream of.

John opened his betway account in 2015, joined the Mega Moolah, and won the record-breaking €17.8 million (about $21.2 million) in less than half an hour.

37. Anonymous gambler - wins $21.3 million

A $10 deposit wins an anonymous gambler $21.3 million

Name: Anonymous
Amount won: $21.3 million
Bet amount: $10
Type of bet: Casino‍
Game: Megabucks slot machine

Could you imagine taking a single spin on the Megabucks machine and winning millions? An anonymous man from Illinois didn’t have to imagine that in 1999. Visiting Caesar’s Palace and placing just a $10 deposit, this man immediately hit the jackpot and won $21.3 million! Talk about luck…

38. Johanna Heundl - wins $22.6 million (about £16 million)

A single spin wins Johanna Heundl $22.6 million

Name: Johanna Heundl
Amount won: $22.6 million
Bet amount: $170
Type of bet: Casino‍
Game: Megabucks slot machine

The anonymous gambler from Illinois isn’t the only person to win millions at Megabucks. Johanna Heundl, a 74-year-old retired printer, had the same thing happen to her. As she was on her way to have breakfast, she stopped by Bally’s and decided to test her luck for the first time ever. She deposited $170, a hefty sum for a first-time gambler, and in a single spin received a $22.6 million pay-off!

39. Anonymous gambler - wins €18.9 million (about $22.6 million)

The biggest betting win in online gambling reaches €18.9 million

Name: Anonymous
Amount won: €18.9 million
Bet amount: $0.75
Type of bet: Online betting‍
Game: Mega Moolah slot machine

We can’t talk about the biggest betting wins in history without at least mentioning the biggest online betting win! While most online gamblers join virtual casinos just to pass the time and maybe get a small pay-off every now and again, there’s one lucky person whose life completely transformed after a short time at the online slots.

In September 2018, an anonymous gambler joined the Mega Moolah at the Grand Mondial Online Casino and posted just a $0.75 deposit. In less than 50 spins, they won €18.9 million (about $22.6 million), breaking all records in online gambling and easily surpassing John Heywood’s win.

40. Anonymous gambler - wins $27 million

From a $680,000 win to $27 million in a matter of months

Name: Anonymous
Amount won: $27 million
Type of bet: Casino‍
Game: Megabucks slot machine

Most people see even small gambling victories as free money, but some see them as alternative investment opportunities. After winning $680,000 at the Wheel of Fortune gaming machine, one 60-year-old lady decided to take her winnings up a notch and invest in her newfound gambling hobby.

After her victory, this woman became a regular at various gambling venues and continued testing her luck. Eventually, her commitment paid off when she hit the jackpot at the Megabucks slots and won $27 million!

41. Cynthia Jay-Brennan - wins $34.95 million

Luck runs out for $34.95 million jackpot winner Cynthia Jay-Brennan

Name: Cynthia Jay-Brennan
Amount won: $34.95 million
Type of bet: Casino‍
Game: Megabucks slot machine

Unfortunately, not all of the biggest betting wins in history have a happy ending. Cynthia Jay-Brennan sat down at the Megabucks Slot Machine during her mother-in-law’s birthday party in 2000. Within just a few minutes, Cynthia won the jackpot, receiving $34.95 million, the biggest-ever Megabucks win at the time.

She gave her two weeks notice the following day, had her dream wedding that she was saving up for, and went to Fiji for her honeymoon. Being kind-hearted, she loaned some money to all of the acquaintances that reached out to her after her victory, and she even started setting up trust funds for all of her family members and in-laws and paying off any debts that they had.

Her luck ran out, however, when a drunk driver rear-ended her a few weeks after her life-changing win. Her sister died in the car accident while Cynthia was left paralyzed from the chest down.

After the accident, Cynthia decided to give back to those in need, so she partnered with the Free Wheelchair Mission and donated thousands of wheelchairs to patients who couldn’t afford them. She’s also donated to the Mothers Against Drunk Driving foundation and given contributions to several schools across Nevada so that they could establish Students Against Drunk Driving clubs.

42. Anonymous gambler - wins $39.7 million

Killing time wins a 25-year-old $39.7 million

Name: Anonymous
Amount won: $39.7 million
Bet amount: $100
Type of bet: Casino‍
Game: Slot machine

Massive wins sometimes come so easily. An anonymous 25-year-old was bored waiting for his basketball game to start, so he headed to the Excalibur casino to pass the time. He placed a $100 deposit and casually started playing video slots. Before long, he won the jackpot and received a $39.7 million pay-off against the odds of 16.7 million/1.

Instead of taking all of the money at once, he made a deal with the casino to receive $1.5 million annually over the following 25 years.

43. Kerry Packer - wins between $20 and $40 million

Billionaire Kerry Packer takes between $20 and $40 million in Las Vegas

Name: Kerry Packer
Amount won: $20 to $40 million
Type of bet: Casino‍
Game: Baccarat and blackjack

How come the rich just keep getting richer, no matter what they do? Before the turn of the century, Australian billionaire Kerry Packer decided to try his luck at baccarat and blackjack, accumulating several astonishing wins in a single evening. It’s estimated that he took anywhere between $20 million and $40 million – the exact figure is unknown since he had quite a few wins over the course of the evening.

Following his astonishing winning streak, Kerry started splashing his money around Vegas, going so far as to tip his head waiter and waitress in the vicinity of $1 million.

However, even Packer couldn’t sustain his winning streak for too long. By 1999, his gambling hobby had cost him about $28 million in London.

44. Gloria McKenzie - wins $590.5 million

Gloria McKenzie sets the record in the Powerball lottery with a $590.5 million win ‍

Name: Gloria McKenzie
Amount won: $590.5 million
Type of bet: Lottery
Game: Powerball‍
Odds: 175 million to 1

Last but certainly not least, among the biggest betting wins in history is Gloria McKenzie and her Powerball pay-off. In 2013, 84-year-old Gloria achieved the highest single winning record in Powerball history and took home $590.5 million, beating the odds of 175 million/1.

Instead of accepting her full prize in 30 monthly instalments, Gloria decided to cash in her prize immediately, so she received only half of the money (still more than enough for any single person).

According to a rumor, Gloria was waiting in line to buy her ticket when the person in front of her let her cut in.

Biggest betting and gambling wins [Infographic]

Conclusion

There’s no single key to success when it comes to gambling and betting. Sometimes, it’s all just a matter of luck, and sometimes you need skill and well-thought-out strategies to succeed. The pay-off is never guaranteed, but it’s always possible. So, bet wisely, and don’t risk more than you can afford to lose.

Sources:

https://www.thepunterspage.com/biggest-sports-betting-wins/

https://www.lineups.com/betting/top-10-biggest-sports-betting-wins-of-all-time/

https://www.mentalfloss.com/article/26275/6-biggest-vegas-wins-history

https://bovegas.com/blog/big-wins/the-biggest-casino-wins-of-all-time/

https://www.translationroyale.com/the-12-biggest-casino-wins-of-all-time/

https://listverse.com/2014/05/10/10-crazy-huge-gambling-wins/