While the chances of landing a big win are always slim, sometimes lady luck shines her smile down upon you – which could see you walk away with enormous winnings.

There are sports bettors whose troubles paid off and landed some of the biggest sports betting wins, which is the basis of our discussion on this page.

These are the stories of some of the luckiest sports bettors in history, who won life-changing amounts of cash.

15. Richard Hopkins – wins $165,000

In 1998 Richard Hopkins took his son, Evan, go-karting, which is where he witnessed young Lewis Hamilton’s driving skills. He was so impressed with this young chap’s skills around the track that he was unequivocally convinced he was going to be a star someday.

Richard went on to make three separate wagers on Hamilton. His initial wager was $200 that his young man would win the Formula 1 before turning 23. He further placed a $100 bet that he would go on to be the World Champion by the age of 25. To further cement his confidence in Hamilton, he made an additional wager of $50 on both initial bets, that this chap would achieve both accomplishments. This gave him odds of 1,500/1.

It took almost 10 years, but Richard’s predictions paid off in a big way. At the age of 22 years, Hamilton won the Canadian Grand Prix in 2007, and the following year he won first place in the Brazilian Grand Prix 2008 at 24. Altogether, the bets yielded a win of $165,000 for Mr. Richard Hopkins.

14. Erick Lindgren – wins $340,000

Erick Lindgren is second on our list of the biggest sportsbook wins – and his story is quite interesting. Being a professional poker player, you would expect him to win in a game of poker. However, Erick won in a game of golf.

Several professional players made a wager; that Erick wouldn't manage to play four straight lines of golf within a single day, in the scorching Las Vegas summer heat, and with his clubs on the back. Precisely, they bet that he would never shoot below 100 in each round, but as luck would have it, Lindgren was smiling to the bank by the end of the day with a $340,000 win.

13. Three Friends Took Over $375,000 on NBA Basket Parlay

In January 2022, a group of three buddies from the state of Pennsylvania bet the same six-leg parlay, which saw them pocket a combined win of $375,000 with just a stake of $1.50.

The bet slip comprised six players to score the first basket of every single match in the nine-game NBA schedule. It was created by Abdul Murphy Jr from East Stroudsburg, who would then send the slip to his other two friends. His buddies didn’t waste time to tail it and they came away with a six-figure payout, a decision we are sure they’re grateful for to this day.

12. Phil Mickelson Won $560,000

Phil Mickelson is another winner on our biggest sports betting wins list. The professional golfer was a big fan of the Baltimore Ravens way before they made a name for themselves in 2000. Phil saw the talent and potential of the team and we can indeed say that his judgment was excellently placed.

He went ahead and placed a bet of $20,000 against the odds, and shortly after it paid back incredibly well. He won a whopping $560,000 from this wager.

11. Mick Gibbs – Wins $700,000

In 2001, Mick Gibbs, a roofer residing in Staffordshire, England, wagered a $2.54 bet on a 15-leg accumulator bet. If you're an avid punter, you know that this is a very hard bet to hit. Particularly, since all legs must be successful for the bet to win. Mick’s bet slip consisted of a mix of horse racing and football events.

Mick had no idea that this bet would be the one to put his name in the news headlines – and also didn’t know how much his payout would be until he went to claim his winnings.

10. Mike Futter – Betting His Horse Brought Him $800,000

Futter is among the biggest winners in sports betting. This is a renowned name in the industry and he also has a story to tell. In 2003, Futter made a wager on his own horse named Manty’s Pass.

Manty’s Pass didn’t disappoint his master as he won first place in the race, earning Futter over $400,000 as the owner. He received an additional $400,000 for his bet, totaling to over $800,000. Even though he had some great bets previously, Fatter said that he would never forget that day.

9. Charles Barkley – Wins $800,000

Barkley is not a new name in the sports betting realm. In 2002, he took his place in the Hall of Fame for one of the biggest wins ever recorded in the NBA.

He placed a bet on the underdogs in the Super Bowl; that the New England Patriots would win against the St. Louis Rams. He also wagered an extra $50,000 on the moneyline, and both bets won.

This win caused a stir as there were reports that Barkley did not have enough credits at his sportsbook, the Mandalay Bay to cover both bets. There were a few back-and-forth deliberations but later got his $800,000 payout.

8. Fred Craggs – Staking $1 Million With a $0.50 Bet

Craggs from Yorkshire is next on the biggest sports betting wins in history. On his birthday, the 60-year-old gentleman decided to make a wager on an 8-horse accumulator with odds at 2,800,000/1.

He staked $0.50 on this bet without a clue that this would be the wager to completely change his life. Each horse on the accumulator won earning him $1 million. What’s funny is that Craggs only knew about the massive win when he went to place another bet at his bookie, which was totally unrelated to the winning bet.

7. Michigan NASCAR Bettor Lands $1 Million

In 2022 August, a lucky punter from Michigan landed a big win with a $13.49 free bet, making headlines across the country.

The NASCAR parlay bet was placed at FanDuel Sportsbook and consisted of four drivers, namely Cody Ware (+2000), David Ragan (+950), B.J McLeod (+2000), and Landon Cassill (+1500). He wagered that each driver would finish in the top 10 of the Coke Zero Sugar 400 in Daytona Beach.

The bet won when David Ragan crossed the finish line in the ninth place, awarding the bettor $999,433.63.

6. James Adducci – A Large Bet Brought $1.2 Million

One of the largest bets ever won goes to James Adducci, who made a wager worth $85,000 on the famous golfer, Tiger Woods in 2019. It was a brave move by this gentleman on account that it was Wood’s first championship in 11 years.

While most people might think it was a bad move, it paid off in a big way, more precisely, to the north of $1.2 million.

5. Steve Whiteley –Betting $2 for Impressive Win of $1.5 Million

In 2011, a guy named Steve Whiteley got a free ticket to go and watch the horse races and he made the wise decision of not missing the event. He then placed a $2 bet on the six winners for that day. He even wagered on a horse that had lost all of the 28 past races. So, he probably wasn’t expecting much from this bet, but to his astonishment, he won a massive $1.5 million.

4. Dave Oancea – Wins $2.5 Million

Dave Oancea landed two of the biggest sports betting wins. He was an avid gambler from Las Vegas a.k.a The Neon City and was on a roll in November of 2015, winning $2.5 million. His first triumph came when he walked away with $200,000, and that’s not even the highlight of the day.

Dave then took his first winnings and made a wager of $140,000 on the Kansas City Royals in the World Series. Placing this bet wasn’t easy and he was forced to spread it across 15 casinos. It turned out, that luck was on his side as the Kansas City Royals thrashed the New York Mets, giving Dave his second big victory of $2.5 million.

3. Marco Piemonte Won $2.8 Million on Parlay Bet

During the 2022 NFL, Marco landed an unbelievable win of all time. His five-leg parlay bet gave him a win of $2.8 million, thanks to the greatest comeback in NFL history.

The wager was made on DraftKings Sportsbook for a stake of $31,000. The bet slip comprised of Browns beating the Ravens, Minnesota Vikings winning against the Colts, Jaguars +4 Vs. the Cowboys, Dolphins +7 Vs. the Bills, and the Raiders beating the Patriots.

2. Billy Walters – Hitting $3.5 Million on the Super Bowl

A gentleman known as Walters is among the biggest bet winners having won $3.5 million during the 2010 Super Bowl. He was a reputable poker player who often recorded amazing wins, indicating winning in gambling isn't solely dependent on luck but also on skill.

He made an impressive wager in the 2010 Super Bowl on the New Orleans Saints to beat the Indianapolis Colts. His pick was the underdog as the Colts seemed unbeatable by all accounts. However, the Saints beat the Colts, which was the first-ever win against the Indianapolis Colts in the Super Bowl.

1. Mattress Mack Hits $75 Million in 2022

71-year-old Mack, whose real name is Jim Mclngvale, and the owner of the Gallery Furniture retail chain is on the biggest sports betting wins list too. He made a sequence of bets on the Houston Astros to beat the Philadelphia Phillies in the World Series, which amounted to roughly $10 million.

He made his bets during the 2022 MLB season at multiple sportsbooks such as Barstool, Caesars, and Wynn. His high-roller bet paid off when the Astros defeated the Phillies in six matches, earning him over $75 million.

There are many legal US sportsbooks that punters can visit to try their luck and possibly land massive winnings. Some of the biggest wins in betting history have been recorded at these bookies.

For example, in 2022 NFL, DraftKings paid out a huge win of $2.8 million to Marco Piemonte as we indicated earlier on this page.

Caesars also paid out enormous winnings to Mattress Mack, who won more than $75 million during the 2022 MLB season.

We’ve also seen that FanDuel recorded a huge payout of close to $1 million, won by a NASCAR bettorin Michigan.

Other sports betting sites known to have recorded great wins in America are BetMGM, BetRivers, and Borgata.

Even the most seasoned punters with the biggest bankrolls don’t always win. You can employ well-laid-out strategies and approaches but still lose. Winning mostly rides on luck and at times skill, to increase your chances of hitting a win. However, in sports betting, a win is never guaranteed. Therefore, always bet wisely and never go above your budget.

The biggest win in betting history is $75 million resulting from a series of bets.

Jim (Mattress Mack) owner of Gallery Furniture in Houston is the man who holds the biggest sports betting win.

While it's unlikely to become rich from gambling, a few people have won a life-changing amount of money.

Billy Walters is renowned as the most successful sports punters. The Las Vegas businessman won hundreds of millions in an unparalleled 36-year winning streak, starting 1980s to 2017.

There is a list of big upsets in betting history but the biggest one has got to be the Leicester City Foxes winning the Premier League in the 2015/16 season. At the start of the season, this team was not seen until 13th on the odds board at +500000.   

WRITTEN BY David Camilleri View all posts by David Camilleri

David is a sports fanatic with a particular interest in stats and figures. When not writing about sports, you would probably find him playing or watching football, researching stats or sharing the latest news with anyone willing to listen.

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