Biggest Bets Ever Won

Biggest Bet Ever Won

Today’s sports betting industry is bigger than ever, with millions of punters from across the globe placing bets on their favorite sporting events daily. Undoubtedly, the primary reason most, if not all, of these bettors enjoy sports betting is the opportunity to win a life-changing amount.

While most of us daydream about hitting a windfall one day, a few lucky punters have recorded the biggest bet ever won.

This guide explores the world of biggest betting wins, covering the following areas:

  • A list of all-time biggest sports betting wins
  • Things to keep in mind when aiming for big bet wins
  • Betting sites with the highest maximum payouts in 2024
  • What do these biggest wins mean for you

List of All-Time Biggest Sports Betting Wins

An indisputable fact about the betting industry is that, more often than not, the odds are against you. It is especially so when you target markets with enormous odds or combine multiple wagers into a single accumulator for massive wins. The chances of winning such bets are usually slim, even for the sharpest bettors. But of course, there is always a possibility. 

With their skills and Lady Luck by their side, many punters have achieved the incredible feat of hitting massive wins, making history with the biggest sports bets ever won in sports betting. Let’s check out some of these all-time most substantial sports betting wins.

Adrian Hayward – £25,000 on a £200 Bet

  • Winner’s name: Adrian Hayward
  • Amount won: £25,000
  • Bet amount: £200
  • Type of bet: Single wager
  • Game: Football (Xabi Alonso to score from behind the halfway line)‍
  • Odds: 125 to 1
Adrian Hayward Wins the Biggest Bet

Getty Images

There is no denying that sports betting requires luck; however, there is a lot of room for experienced punters to use their knowledge to analyze players, their skills, and perceived chances of winning to make predictions. And that’s precisely what Adrian Hayward did when he raked in one of the biggest football bet wins in 2006.

As an avid Liverpool fan and supporter for over 26 years, Hayward quickly noticed that his team’s midfielder, Xabi Alonso, had been attempting to score from his half several times the previous season. He knew that Xabi would eventually score a goal from there at some point during the season and decided to put a £200 bet on it on Paddy Power, though the odds were against him at 125 to 1.

Xabi Alonso didn’t disappoint him and scored a goal from behind the halfway line in the closing minutes during a Liverpool match against Luton Town in the FA Cup’s third round. The goal led to a 5-3 win for Liverpool, and Adrian received a £25,000 payout, one of the biggest bets ever won.

Anonymous Bettor – $76,000 on a $0.10 Bet

  • Winner’s name: Anonymous
  • Amount won: $76,000
  • Bet amount: $0.10
  • Type of bet: Single superfecta wager
  • Game: Horse racing (Superfecta)‍
  • Odds: 88 to 1

Nobody would have ever imagined that an amount as little as $0.10 could result in one of the biggest betting wins. Two anonymous punters in Saratoga Springs, USA, made that happen with a Superfecta horse race bet and managed to rake in $76,000.

The punters put action on a high-risk Superfecta wager, which refers to making predictions on the first four horses that will finish in a race and the exact order they will come in. As you can imagine, this is a hard market to predict, resulting in pretty attractive odd prices of 88/1. Surprisingly, the two Saratoga Springs punters managed to beat the odds, and their forecast proved accurate, resulting in $76,000 in profits, one of the biggest single bets won in horse racing.

Tayla Polia – $105,000 on a $5 Bet

  • Winner’s name: Tayla Polia
  • Amount won: $100,005
  • Bet amount: $5
  • Type of bet: Accumulator
  • Game: American football (15-leg parlay on NFL)‍
  • Odds: 20,000 to 1

There is no denying that parlays, also known as accumulators, are by far one of the riskiest forms of sports betting available online as they involve multiple sports selections. Parlay bets require that every prediction within the wager is accurate for you to win – which makes Tayla Polia’s accumulator win pretty amazing.

Tayla Polia decided to take a chance on a 15-leg parlay wager in the NFL on William Hill’ sportsbook, featuring handicap wagers on nine favorites, five underdogs, and one over/under market. The bookmaker offered an unbelievable 20,000/1 odds on the parlay, and she staked just $5 on it.

From the combined odds of the bet, it’s easy to see that this is a pretty long shot wager, but surprisingly, Polia’s decision paid off, and every one of her selections proved correct. It resulted in a payout of $100,005 in winnings, making it one of the biggest parlay bets ever won. The most surprising thing about this incredible win is that although she had been a lifetime sports fan, this was the second time Polia had ever placed any bet.

Gerry Mcllroy – £100,000 on a £200 Bet

  • Winner’s name: Gerry Mcllroy
  • Amount won: £100,000
  • Bet amount: £200
  • Type of bet: Single wager
  • Game: Golf (Rory Mcllroy to win British Open within a decade)
  • Odds: 500 to 1
Gerry McIlroy Wins the Biggest Bet

Daily Mail

Not every day you find a family member who has complete faith in an athlete’s skills and decides to put money where their mouth is. And that was what Gerry Mcllroy did in 2004 when he confidently made a wager on his son to win the British Open within a decade, a decision that resulted in one the biggest sports bet win ever.

At the time, Mcllroy’s son, the golfer Rory Mcllroy, was only 15 years old, but he was confident in the boy’s growing skills. So, Mcllroy displayed his incredible foresight by placing a £200 wager on the bet at Ladbrokes, who offered a 500-1 odds price on the market. Rory Mcllroy soon met his father’s expectations within a few years when he beat Spain’s Sergio Garcia and U.S. Rickie Fowler to win the British Open. As a result, the dad managed to rake in £100,000 in winnings from Ladbrokes.

Interestingly, following in Gerry’s footsteps, his son’s friends also decided to bet on Rory’s golfing skills, resulting in them raking in £80,000.

Nicholas Newlife – £101,840 on a £1,520 Bet

  • Winner’s name: Nicholas Newlife
  • Amount won: £101,840
  • Bet amount: £1,520
  • Type of bet: Single wager‍
  • Game: Tennis (Roger Federer to win seven Wimbledon tournaments)
  • Odds: 66 to 1
Nicholas Newlife Wins the Biggest Bet

Daily Mail

Another impressive big bet win that rightly predicted a future occurrence is Nicholas Newlife’s wager. Back in 2003, like many other tennis fans, Newlife was impressed by Roger Federer’s skills during the Wimbledon tournament. Anticipating that the player would achieve future successes, Newlife placed a £1,520 bet with bookmaker William Hill on Federer to win seven Wimbledon tournaments.

His dream came true almost a decade later when Federer won his seventh Wimbledon, resulting in the bet paying off with £101,840 (approximately $186,000) in winnings. Unfortunately, Newlife didn’t live to see this day and his biggest bet win ever, as he had already passed away in 2009. Newlife’s belongings and the big prize win were donated to Oxfam International, a charity that fights global poverty.

Peter Edwards – £125,000 on a £50 Bet

  • Winner’s name: Peter Edwards
  • Amount won: £125,000
  • Bet amount: £50‍
  • Type of bet: Single wager
  • ‍Game: Football (Harry Wilson to play for Wales)
  • Odds: 2,500 to 1

Peter Edwards is another person who made a prediction far into the future, resulting in one of the biggest sports bets won. Fifteen years before this win, Edward dreamed that his then 18-month-old grandson Harry Wilson would become a professional football player who would one day represent Wales. He then placed a £50 bet on his dream at his local William Hill sportsbook.

Surprisingly, his dream came true in 2013 when Harry Wilson made his international debut as a substitute player for the Wales National team in a match against Belgium at 16. This inspiring wager resulted in a payout of £125,000 for his grandfather, who collected his winnings and happily retired soon after.

Dave Oancea – wins $200,000

  • Winner’s name: Dave Oancea
  • Amount won: $200,000
  • Bet amount: $20,000
  • Type of bet: Single wager
  • Game: UFC‍ (Holly Holm to beat Ronda Rousey)
  • Odds: 11 to 1

Dave Oancea, also known as Vegas Dave, is a renowned gambler in Las Vegas known for recording two of the biggest sports bets ever won in weeks. The first of the two wins happened with the UFC 13, where Oancea placed a $20,000 wager on the underdog Holly Holm to beat Ronda Rousey at 11 to 1 odds.

Many punters would have said that Oancea’s wager that day was foolish, especially with that kind of money. However, the fight proved him right as Holly Holm won shockingly, netting a massive $200,000 winnings. We will discuss Oancea’s second-biggest-ever bet win later.

Mick Gibbs – £157,000 on a £2.50 Bet

  • Winner’s name: Mick Gibbs
  • Amount won: £157,000
  • Bet amount: £2.50
  • Type of bet: Accumulator
  • Game: Football (9-leg accumulator)
  • Odds: N/A

Our list would no doubt be incomplete without mentioning Mick Gibbs, a punter with one of the biggest multi-bet wins ever in the UK. A roofer by profession in Staffordshire, Gibbs has proven to have an eye for winning accumulator wagers on two notable occasions.

His first big win came at the turn of the century in 1999 when he forecast nine football games across Europe and placed a tiny sum of £2.50 on them as a parlay wager. Gibbs’s nine-leg accumulator predictions proved accurate, earning him £157,000 in winnings, a figure the punter soon topped with another impressive accumulator wager. We will discuss that later.

Richard Hopkins – £165,000 on several Bets

  • Winner’s name: Richard Hopkins
  • Amount won: £165,000
  • Bet amount: £350
  • Type of bet: Multiple single wagers
  • Game: Formula 1‍ (Lewis Hamilton to win the Grand Prix and World Series before 25)
  • Odds: (300/1, 500/1, and 1,500/1)

When Richard Hopkins, a Peterborough resident, took his son for go-kart racing in 1998, little did he know he would meet young Lewis Hamilton, who would later become one of the most excellent Formula 1 drivers ever. Even at 13, Hopkins was greatly impressed by Hamilton’s skills behind the wheel, and he knew the boy had potential for greatness.

It convinced Hopkins to place a futures bet of £200 on Hamilton winning the Grand Prix at the age of 23, offered to him at 300/1 odds. Soon after, Hopkins placed another £100 on Hamilton winning the World Championship by 25, offered at 500/1 odds. Confident of the young boy’s skills, he placed an additional £50 on both predictions together at 1,500/1.

It took almost a decade, but Hamilton ended up winning his First Formula 1 World Championship as Hopkins predicted, earning him a massive big bet win of £165,000.

Anonymous punter – $250,000 on a $8,500 Bet

  • Winner’s name: Anonymous 
  • Amount won: $250,000
  • Bet amount: $8,500
  • Type of bet: NFL accumulator‍
  • Game: American football (5-leg accumulator)
  • Odds: N/A

Another anonymous punter made the list of the largest sports bet ever won by hitting five legs on a parlay. This unnamed bettor placed this wager at the MGM Resorts sportsbook in Las Vegas with five legs during an NFL weekend featuring the Ravens, Patriots, Chiefs, Raiders, and Detroit Lions. Feeling confident with his bets, the unnamed bettor staked $8,500 on the accumulator wager.

After four correct predictions, the Detroit Lions also ended up victorious by beating the New York Giants with a 24-10 score in the fifth and final leg. It resulted in the punter winning $250,000 in profits, becoming one of the biggest sports bets ever won.

Anonymous Punter – £200,000 on a £100 Bet

  • Winner’s name: Anonymous bettor
  • Amount won: £200,000
  • Bet amount: £100
  • Type of bet: Single outright wager
  • Game: Football futures (Leicester City to win English Premier League)‍
  • Odds: 5,000 to 1

Leicester City’s victory in the 2015 Premier League is undeniably one of the most shocking league victories that will not be soon forgotten. Not many could have imagined that the team just promoted from relegation would triumph over all the other teams and win the league. Even bookmakers put a 5000/1 odds on the wager, showing how unlikely they think the outcome would happen. 

However, one anonymous punter didn’t mind taking these longshot odds and placed a £100 bet on Leicester winning the English Premier League. Shockingly, Leicester City made history that season and took the victory, leaving the anonymous bettor £200,000 richer as one of the biggest-ever bet wins. Interestingly, another punter, Leigh Herbert, placed a mere £5 on the same odds while on holiday, netting him a sum of £20,600.

Anonymous punter – $305,375 on a $5 Bet

  • Winner’s name: Anonymous
  • Amount won: $305,375
  • Bet amount: $5
  • Type of bet: Accumulator‍
  • Game: Basketball (12-leg parlay)
  • Odds: N/A

In 2016, another bettor in Las Vegas pulled another big bet win with a basketball parlay wager. The anonymous punter correctly selected 12 basketball game winners on a parlay card for one weekend. He did this at the William Hill sportsbook with only a $5 participation fee.

Since his selections panned out as predicted, the Las Vegas anonymous bettor raked in $305,375, making it one of the highest big accumulator wins.

Erick Lindgren – $340,000 on a Bet Placed by Other Professional Players

  • Winner’s name: Erick Lindgren
  • Amount won: $340,000
  • Bet amount: N/A
  • Type of bet: Sports betting ‍
  • Game: Golf (personal bet between Erick Lindgren and his friends)
  • Odds: N/A
Erick Lindgren Wins the Biggest Bet

Upswing Poker

An unorthodox big bet win that made our list is Erick Lindgren’s crazy wager with his friends, all professional poker players. This professional poker player made a novelty bet with his friends on a personal golf game, which kept escalating. The condition of the wager was that Erick had to play four consecutive rounds of golf on a single day. He also had to do this while carrying his clubs and shooting below 100, under 100+ degrees in the Las Vegas heat. Looking like a challenging task, his friends bet against him with their wager totaling $340,000.

Surprisingly, Erick Lindgren came out on top and finished the game in over 14 hours. Although he lost about 15 pounds and suffered heat stroke and dehydration for his efforts, he walked away $340,000 richer.

Anonymous punter – $375,000 on a $500 Bet

  • Winner’s name: Anonymous
  • Amount won: $375,000
  • Bet amount: $500
  • Type of bet: Two single wagers‍
  • Game: MLB baseball (St. Louis Cardinals to win National League and also win World Series)
  • Odds: N/A

Fans placing bets on their favorite teams is nothing new in the sports betting scene. However, this doesn’t always lead to a successful bet, least of all, big betting wins. An anonymous St. Louis Cardinals fan didn’t seem to mind when he placed a $250 wager on his team winning the National League. He then backed them to win the World Series with another $250 wager. At the time, the Cardinals were nowhere near the favorite for the win, but they soon started winning games consistently.

The anonymous bettors’ predictions came true as the St. Louis Cardinals became the unlikely World Series Champion, resulting in one of the biggest sports bets ever won with $375,000 in winnings.

Phil Mickelson – $560,000 on a $20,000 Bet

  • Winner’s name: Phil Mickelson
  • Amount won: $560,000
  • Bet amount: $20,000
  • Type of bet: Single outright wager
  • Game: NFL American football (Baltimore Ravens to win the Super Bowl XXXV)
  • Odds: 22 to 1

Phil Mickelson, known as one of the best golfers of all time, is also a sports betting enthusiast and an avid fan of the Baltimore Ravens. Seeing the team’s growing strength and talent leading up to the 2000/2001 NFL season, Mickelson decided to wager on the Baltimore Ravens winning the Super Bowl at 22/1 odds. He made a betting syndicate and placed a $20,000 stake at 22/1 odds on the outcome.

Surprisingly, his prediction proved true when the Ravens beat the New York Giants by 34-7 to win the Super Bowl XXXV, resulting in one of the biggest bets won by a golfer with $560,000 (around £426,000) in profits.

Mick Gibbs – £500,000 on a £0.30 Bet

  • Winner’s name: Mick Gibbs
  • Amount won: £500,000
  • Bet amount: £0.30
  • Type of bet: Accumulator
  • Game: Football‍ (15-leg parlay)
  • Odds: 1,666,666 to 1 (combined acca odds)

Not too long after winning £157,000 in a 9-leg parlay bet, the English roofer Mick Gibbs managed to secure another biggest odds bet ever won a second time with another tiny stake in 2001. This time, Gibbs placed a £0.30 bet on a 15-leg accumulator featuring predictions on different games in the Champions League. The combined odds of these parlay selections stood at an insane value of 1,666,666/1, making it a seemingly unlikely outcome.

Surprisingly, all of Gibbs’ predictions proved correct, winning him an astonishing figure of £500,000. Having received this payout from only £0.30, this is undoubtedly one of the most unique, biggest sports bets ever won.

Darren Yates’ Magnificent Seven – £550,000 on a £62 Bet

  • Winner’s name: Darren Yates
  • Amount won: £550,000
  • Bet amount: £62
  • Type of bet: Sports betting
  • Game: Horse racing (Frankie Dettori to win seven out of seven races in the Royal Ascot)
  • Odds: N/A
Darren Yates Wins the Biggest Bet

The US Sun

There is no denying that winning all races they are a part of on a race day is an incredible achievement that any jockey would want to make. Frankie Dettori made one of the most iconic moments in horse racing history by achieving this feat in 1996 at the Ascot by winning seven out of seven races. This feat was dubbed the “Magnificent Seven.”

However, Dettori wasn’t the only winner that day as one punter in particular met a life-changing windfall. Darren Yates, a businessman, horse racing enthusiast, and gambler, had placed a £62 bet on Dettori to win all seven of his races that day at the Ascot with William Hill. No one could imagine Frank Dettori winning all seven races, which he did, resulting in one of the most surprising and largest bets ever won in horse racing. Darren Yates took home £550,000 that incredible day.

Anonymous Punter – £585,000 on an £0.80 Bet

  • Winner’s name: Anonymous
  • Amount won: £585,000
  • Bet amount: £0.80
  • Type of bet: Accumulator
  • Game: Football (19-leg parlay)‍
  • Odds: 683,738 to 1 (combined acca odds)

Another unlikely wager turned into one of the biggest parlay bets ever won happened when an anonymous bettor from Malta put action on a 19-leg accumulator in 2011. This anonymous punter picked 19 selections, combined them into an accumulator wager with 683,738-1, and staked just 80 pence. Despite the longshot nature of the parlay wager, all of the predictions were on point, ending with Liverpool scoring a last-minute winning goal in a match against Chelsea. These unbelievable big accumulator wins resulted in the bettor walking home with a massive sum of £585,000.

Charles Barkley – $800,000 on a $500,000 Bet

  • Winner’s name: Charles Barkley
  • Amount won: $800,000
  • Bet amount: $500,000
  • Type of bet: Single futures
  • Game: NFL American football (New England Patriots to win the Super Bowl XXXVI)

NBA superstar Charles Barkley is one of the many sports athletes who enjoy trying out their hand at sports betting and has had some success stories. However, he recorded his biggest sports bet ever won when he placed an astonishing $500,000 bet on the New England Patriots winning the Super Bowl in 2002.

Interestingly, aside from the extremely colossal amount Barkley risked on the bet, the New England Patriots were the 14-point underdog against St. Louis, making it a risky endeavor. Fortunately for Barkley, his prediction proved accurate, and he won $800,000 as one of the biggest underdog bets ever.

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

  • Winner’s name: James Adducci
  • Amount won: $1.2 million
  • Bet amount: $85,000
  • Type of bet: Single wager
  • Game: Golf (Tiger Woods to win the 2019 Masters Tournaments)
  • Odds: 14 to 1

There is no denying that James Adducci’s wager on Tiger Woods is one of the gutsiest largest bets ever won. Although Tiger Woods is undeniably one of the best professional golfers in the world, he had fallen into a slump at some time. By 2019, it had already been 11 years since Woods’ last championship victory in the Masters, resulting in him being nowhere near the bookies’ favorite.

Surprisingly, a gutsy punter, James Adducci, decided to place an $85,000 bet on Tiger Woods winning the Masters Tournaments that year on William Hill at odds of 14-1. It was a risky wager, but Adducci’s brave initiative shockingly paid off when Woods broke his 11-year-long dry spell and won the Masters Tournament. He got a massive payout of $1.2 million, which broke William Hill’s record for the largest bet ever won for futures.

Mike Futter – £800,000 on Betting His Horse

  • Winner’s name: Mike Futter
  • Amount won: £800,000
  • Type of bet: Single wager‍
  • Game: Horse racing (Monty’s Pass to win at Grand National)

Mike Futter, an Irish bingo hall owner, is another name that raked in one of the biggest bets ever won in horse racing. In 2003, the punter placed a bet on Monty’s Pass, which also happened to be his horse, to win at the Grand National at Aintree. The horse did not disappoint its owner and proved the prediction true. With this win, Futter received £348,000 as Monty’s Pass owner and an additional £400,000 for the successful bet.

After the successful wager, Futter admitted that while he has had some fantastic bets and days, this is one he will never forget. It is undeniably one of the biggest horse racing bets ever won.

Fred Craggs – £1 million on a £0.50 Bet

  • Winner’s name: Fred Craggs
  • Amount won: £1 million
  • Bet amount: £0.50
  • Type of bet: Accumulator
  • Game: Horse racing‍ (8-leg parlay)
  • Odds: 2,800,000 to 1 (acca combined odds)
Fredd Craggs Wins the Biggest Bet


Another monumental horse racing bet win happened when fertilizer salesman Fred Craggs placed an incredible eight-leg accumulator wager on horse races. In 2008, the Yorkshireman Craggs just walked into his local William Hill shop, picked eight horses carefully, and placed a 50p accumulator on them.

The combined odds totaled 2,800,000/1, so the Yorkshireman didn’t think much of this wager, not knowing it would earn him a life-changing fortune. Shockingly, his predictions proved true, earning him £1 million in winnings and the biggest odds bet ever won on our list.

Interestingly, Craggs had no idea that his wager had won until he returned to William Hill to place a new bet. If he had gone with the no-limit bet option, the winnings would have totaled £1.4 million, but the payout was still a million more than he expected. This massive win came on the eve of his 60th birthday and was profoundly shocking news for Craggs and his family.

Steve Whiteley – £1.5 million on a £2 Bet

  • Winner’s name: Steve Whiteley
  • Amount won: £1.5 million
  • Bet amount: £2
  • Type of bet: Accumulator
  • Game: Horse racing (6-leg parlay)
  • Odds: Tote wager

Steve Whiteley, a 61-year-old heating engineer from North Tawton in Devon, managed to land the biggest bet won in horse racing history in 2011. Whiteley, who had received a free ticket to the local horse race track in Exeter, used it to enjoy his day watching horse races. In the spirit of fun, Whiteley picked six winning horses and placed a £2 acca bet on them on the Tote Jackpot.

Surprisingly, Lady Luck was on Whiteley’s side that day as all his picks came out victorious in their respective races, earning him an astonishing £1.5 million in winnings. It is undeniably the biggest bet win in the history of horse racing parlay wagers.

Vegas Dave – $2.5 million on a $140,000 Bet

  • Winner’s name: Dave Oancea 
  • Amount won: $2.5 million
  • Bet amount: $140,000 
  • Type of bet: Multiple single wager‍
  • Game: MLB baseball (Kansas City Royals to win the World Series)
  • Odds: Varied odds ranging from 5-1 to 30-1

After his earlier success of raking in $200,000 in winnings, as mentioned above, Vegas Dave Oancea made another incredible big bet win in 2015. One week into the 2015 MLB season, Oancea placed a heavy wager on the Kansas City Royals to win the World Series. Back then, everybody would have thought him insane as the team was nowhere near the favorite, with most bookies offering 30/1 odds on the wager.

An interesting detail about this wager is that no single casino was willing to take on Oancea’s liability, so he had to spread his $140,000 bet across 15 casinos. Vegas Dave proved his doubters wrong when the Kansas City Royals beat the New York Mets, thereby winning the series. This high-risk wager paid off as one of the biggest bets won, earning Oancea a $2.5 million prize in winnings.

Billy Walters – a successful $3.5 million bet

  • Winner’s name: Billy Walters
  • Amount won: $3.5 million
  • Type of bet: Sports betting‍
  • Game: NFL American football (New Orleans Saints to beat the Indianapolis Colts)

Another name that made it to the annals of the world’s biggest bet win in sports history is Billy Walters. Walters started his betting journey in poker but soon took to sports betting and managed to be successful in it, netting incredible wins and streaks. 

One of his biggest record-worthy wins happened when he decided to get in on the action during the 2010 Super Bowl XLIV. After careful consideration, Walters placed his wager on the New Orleans Saints, the underdog to beat the Indianapolis Colts. Surprisingly, the seemingly unlikely wager panned out for Walters when the Saints claimed their first victory against the Colts, netting him $3.5 million (about £2.7 million) in winnings. Walters’s bet will decrease as one of the largest bets ever won in sports betting.

Mattress Mack Wins $72.66 Million

  • Winner’s name: Jim Mclngvale
  • Amount won: $72.66 Million
  • Bet amount: Series of wagers totaling $10 Million
  • Type of bet: Multiple single wagers
  • Game: MLB Baseball (Houston Astros to win World Series)
  • Odds: Series of odds, including 10/1, 5/1, 5.3/1

The Texas furniture legend Jim Mclngvale, better known as “Mattress Mack,” made a mark when he hit the biggest sports bet win in history. This diehard Houston Astros fan’s relentless approach to gambling has caused him to lose millions betting on the World Series, especially on his team.

As he often does, Mattress Mack placed a series of bets on the Astros to win the 2022 World Series early in the season, including $3 million at Caesars @10/1 odds and $2 million at WynnBet. Later in July, he wagered $2 million on the same bet at BetMGM @5/1 odds, $2 million at Barstool at 5.3/1 odds, and $1 million each on Unibet and Betfred @ 5/1 odds. The wager totaled $10 million, making it a high-risk one.

Shockingly, his unrelenting pursuit paid out this time as the Houston Astros beat the Philadelphia Phillies in six games and won the World Series. Mattress Mack won $72.66 Million that day, the biggest bet win in history. The most exciting part of this win is that, as he has done in most seasons, Mattress Mack used the bet as insurance on his “If Astros win, you win” promotion. So, anyone who has spent $3,000 or more in his store can return for a cashback refund while keeping their item. So, it was a win for many people in Texas.

Biggest Accumulator Betting Wins

Accumulator bets, often called “Accas” or parlays, can bring out life-changing windfalls by combining the odds available on multiple selections into one. Plus, with an accumulator, you won’t necessarily have to place an enormous stake or target insane odds prices to win big.

The downside to acca wagers is that it requires that every selection within the bet wins for you to get a payout. And with most having five or more different selections combined into one, the chances of winning these bets are usually quite slim. As a result, while there have been different smaller wins, there have only been a few big accumulator wins worth mentioning. Let’s explore some history-making wins in this category:

  • An anonymous housewife hits big on the first try: In 2017, an unknown housewife got involved in her husband and son’s passion for football and ended up winning one of the biggest multi-bet wins ever. The housewife picked 12 teams whose names she liked the sound of and decided to place a £1 accumulator wager on them. The seemingly naive acca panned, winning her an astonishing sum of £574,278. It is undeniably one of the most outstanding examples of beginner’s luck in sports betting.
  • The ridiculous in-play accumulator: Accurately predicting the results of eight football matches is a fantastic feat, but predicting the outcomes while the game is already in full swing with only 20 minutes left is a different level. And this is precisely what an anonymous punter from London did by placing £100 on an 8-leg acca bet. The most impressive part is that all his selections were on the losing teams when he placed the wager, resulting in the incredible odds offered. Shockingly and fortunately for the punter, the high-risk gamble paid off, and the teams he picked made an upset and won their games, earning him £650,000 in winnings.
  • BetMGM customer hits: To keep things simple with sports they are familiar with, most accumulator bettors tend to keep their acca wagers on one or two sports. However, in a pretty exciting bet, a customer at BetMGM placed a 15-leg accumulator wager on various sports, including college football, professional football, basketball, ice hockey, and golf. Luckily, all the games came through, resulting in an enormous 1.13 million (£930,000+) winnings for the punter.

Largest Parlay Ever Won

As mentioned, due to the nature of the wager, the chances of winning parlay wager are pretty low, but there have been many incredible big bet wins over the years. However, Steve Whiteley’s incredible £1.5 million jackpot win was the biggest parlay bet ever won. As mentioned, the heating engineer from North Tawton in Devon went to a local horse race track in Exeter after winning a free ticket. Once there, he decided to have some betting fun and placed a £2 Tote jackpot wager on six selections to win their races. Shockingly, all his picks proved accurate, and he landed a windfall of a massive £1.5 million payout.

Sportsbooks and the Biggest Bet Wins Ever

Naturally, a punter must wager with a bookmaker to stand a chance of achieving the biggest bet ever won, or any win for that matter. Back in the day, you would usually need to go to sportsbook stops or horse race tracks to wager on the events you are interested in. Many of the biggest wins on our list went this way.

However, thanks to the emergence of the internet and the technological advances that followed, you can now easily place sports bets online anytime and from anywhere. Both old and new sportsbook brands now provide seamless betting services to punters online, and you will find hundreds of them. These sites even offer promotional incentives to attract new customers or reward existing ones, increasing bettors’ chances of winning.

So, whether you prefer land-based sportsbooks or online betting sites, you can always aim for big wins. Who knows, Lady Luck may decide to smile at you too.

Best Betting Sites with the Highest Maximum Payout in 2024

As mentioned, many sportsbooks provide sports betting services to punters online today. However, some offer higher maximum payouts than others. As expected, these sites are also the ones that have consistently paid out big betting wins to lucky punters who made accurate predictions. 

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That said, some of the best bookies known for the highest maximum payout in 2024 include:

  • William Hill: William Hill is one of the biggest and oldest sportsbooks in the world. It is a reputable brand that provides sports betting to punters online and in land-based shops, with one of the highest maximum payouts in 2024. William Hill is also known to have paid out some of the biggest sports bets ever won, such as Darren Yates’ magnificent seven wager, Fredd Craggs’ eight-leg horse race accumulator wager, and many others.
  • Ladbrokes: Another reputable major player in the sports betting scene known to provide a high maximum payout limit to its customers is Ladbrokes. Gerry McIlroy’s £100,000 payout on the wager he placed on his son to win the British Open came from Ladbrokes. In 2017, a retired man won £457,000 off a 20p bet at Ladbrokes. And in 2022, an unnamed punter also won £505,984 on a £2 wager on an 18-leg accumulator. These are just a few of the numerous big bet payouts the bookie has recorded.
  • BetVictor: BetVictor is another reputable bookmaker with a long history in the sports betting scene. The sportsbook has been consistently paying out some of the biggest betting wins in the industry and still has a high maximum payout limit in 2024. During the 2018 World Cup, an anonymous punter won a massive £1,000,000 using the bookie’s unique #PriceItUp bet builder. In 2019, another lucky bettor scooped up £486,000 in winnings on a £2 Lucky 31 bet.

Other sportsbook that are known to provide big bet payout to their lucky punters includes:

  • Betfred
  • Bet365
  • Skybet
  • Betfair
  • Betway
  • Unibet 
  • etc.

Aside from offering the highest maximum payouts, these sportsbooks feature competitive odds, huge betting markets, several convenient payment methods, helpful customer support, etc.

Payment Methods with the Biggest Betting Wins 

You will agree that one of the most important considerations regarding best live betting prediction sites with the top wins is the payment methods offered. While most bookies will typically provide as many payment options as possible, the methods available usually vary from one platform to the other. So, ensure that the platform you bet on has your preferred payment option before you sign up.

That said, payment methods usually have limits that they can handle regarding how much you can withdraw at any point in time. Also, some bookmakers have different maximum payout allowed for different payment options. For example, the most popular payment methods, like bank cards, typically have higher limits. On the other hand, e-wallets and prepaid cards tend to have lower limits but are usually still quite sizable.

The Impact of Promotions on Maximum Payouts

Promotions and bonuses are a common feature in sports betting. They come in various forms, such as welcome bonuses, free bets, no-deposit bonuses, etc. Bookmakers design these offers to attract and retain customers on their platforms.

Punters can use bonuses and promo offers to significantly increase their chances of winning and potential payouts. These incentives provide additional betting capital, allowing for more bets and exploring different strategies. Therefore, they significantly land huge payouts, especially regarding parlays and accumulators.

However, bookmakers are not in the business of giving out free money, so they often attach terms and conditions to their offers, including maximum payouts. As a result, no matter the odds offered on a bet, a promotion often limits the maximum payout you can get from the wager while using the bonus. For example, you may get a £10 free bet to wager on any sport at a sportsbook, capped at £250. The maximum payout you will get from using the free bet promotion will not exceed £250.

So, before attempting to hit big betting wins with promotions, check out its terms and conditions.

What Do the Biggest Betting Win Examples Mean for Me?

It is possible to win big from sports betting — the list of the largest bets ever won above is evident enough. Let’s examine three distinct ways this can happen.

The first method is to put an enormous stake in a bet with odds that are also big enough. As a result, any winnings you get from the wager would be massive if your prediction proved correct. A typical example is the biggest bet ever won, where Mattress Mack placed a series of bets totaling $10 million on odds prices between 5/1 and 11/1 across different sportsbooks.

The second possibility is to put a decent amount of stake in a single event that sportsbooks perceived to be highly unlikely. With this market, you get a huge odds price that can easily turn into massive winnings with just enough stake and luck by your side. A typical example would be when one of the anonymous punters on our list placed an unlikely wager on Leicester City winning the 2015 Premier League at 5000/1 odds.

The third and last method is to create an accumulator wager, which combines the odds of multiple selections to form a much bigger odd price. Many punters create 5-leg accumulators or more with massive combined odds and place a small stake on it. A typical example is the largest parlay bet ever won mentioned earlier, where Steve Whiteley won £1.5 million on a six-leg accumulator with just £2.

However, you should also know the downsides of each method before trying it for your big bet win. As you might have inferred, the first method is highly risky. Mattress Mack could have easily lost the $10 million stake if the Astros had not won the World Series. The second option, on the other hand, is quite luck-dependent. After all, nobody could have imagined that the fresh from relegation Leicester City would win the league. The third one requires that every prediction you make is accurate to get the big bet win, which also has a longshot chance of winning. So, when skilled bettors aim for big betting wins, use the best method while considering responsible gambling.

Things to Keep in Mind When Aiming for Big Betting Wins

The instances of the biggest betting wins in sports that we have mentioned above have shown that any punter can, through sheer luck and strategic predictions, also achieve something incredible. Here are some valuable tips to remember to improve your chances if you want to hit it big.

Tips Explanation
Choose your bets wisely While luck plays a role in punters getting big betting wins, knowledge and skills are very important. So, ensure you choose your wagers wisely. Research the bets you want to place and stay informed on all the relevant news and updates.
Don’t bet on odds that exceed the maximum payout There are times when sports betting enthusiasts winning are so large that they exceed the maximum payout that a sportsbook allows. It is especially important when considering an accumulator, which usually combines the odds of multiple selections. You could risk your wager by adding extra legs that won’t provide additional value due to the maximum payout. So, make sure only to target value odds.
Be realistic with your wagers You typically won’t get massive returns without tremendous odds or risking an enormous stake amount. You should avoid the latter option if you cannot afford to lose. So, you should be realistic with your wager and enjoy the ride while accepting that losing will always be possible.
Compare different sportsbooks Another essential truth about sports betting is that the odds offered on various outcomes usually vary from bookmaker to book. So, it’s often best to shop around different bookmakers to find the best odds and even more generous bonus and promotional offers.

Final Word

Sports betting is challenging. It is especially true for wagers with enormous odds prices and accumulators capable of triggering big betting wins. However, the likes of Mick Gibbs, Vegas Dave, Steve Whiteley, etc., and their impressive wins show that it can beat the odds and claim shocking windfalls.

Overall, it would help if you never forgot that sports betting generally depends on your knowledge, skills, sound strategy, and luck. A big bet win is never guaranteed but is always a possibility. So, when aiming for substantial betting wins, bet wisely and don’t risk more than you can afford to lose. Do also remember to have fun.

Frequently Asked Questions

  • What is the biggest bet ever won?
    The biggest sports bet ever won was a $72.66 million payout on the Houston Astros to win the 2022 World Series. The bet was placed by an Astros fan and sports betting enthusiast “Mattress Mack” Mclngvale, a furniture store owner in Texas.
  • What is the biggest football bet ever won?
    The biggest bet ever won in football was a £650,000 payout on an 8-leg accumulator wager placed by an anonymous punter in London with a £100 stake. The exciting part about this big bet win is that all the selected eight games were live matches with about 20 minutes to go, and each team was on the losing end.
  • What is the biggest single football bet ever won?
    The biggest single football bet ever won was £200,000 on Leicester City to win the 2015 English Premier League, placed by an anonymous punter. The most exciting part of this wager is that Leicester City just got promoted from relegation the previous and would not be considered a good bet, evident from the 5000/1 odds many bookies offered on it. Surprisingly, Leicester managed to make history, proving the anonymous bettor right.
  • What is the biggest accumulator win?
    The biggest accumulator bet win was £1.5 million on a 6-leg parlay with a tiny £2 wager on the Tote jackpot. The bet was placed by a heating engineer from North Tawton in Devon, Steve Whiteley, at a race track in Exeter after winning free tickets to watch horse races. Shockingly, the eight horses he had just picked for fun won their races, resulting in a big win.
  • What is the biggest parlay ever won?
    As mentioned, the biggest parlay ever won happened when Steve Whiteley placed a £2 bet on an 8-leg accumulator, winning an astonishing £1.5 million jackpot.
  • Still have questions?
    Ask our experts
Tim E
Betting Guru

Tim is our betting guru. Every gaming site needs one, and Tim’s our guy. He has plenty of experience in betting online and is quite successful at it. Tim’s favorite sports are hockey, baseball, and Esports. Tim believes the latter to be the future of betting.

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