Top 10 Biggest Sports Betting Wins Of All-Time

1. Tiger Woods $85,000 Masters Bet

Tiger Woods is obviously the most accomplished golfer of all-time but recently he hasn’t been a sure-fire bet like he was in the past. That didn’t steer away bettor James Adducci who got his wife to allow him to place an $85,000 wager on Woods to win the 2019 Masters at the William Hill sportsbook with 14/1 odds. It paid off and Adducci brought home about $1.2 million dollars and this payout broke William Hill’s record for the largest paid out future bet. Adducci also claims that this was his first-ever sports wager.

2. “Vegas Dave” Kansas City Royals Future

Most people know “Vegas Dave” from his obnoxious takes and claims about his betting record but the fact of the matter is, he has won some big bets. The one that really put him on the map was when he decided to bet on the Kansas City Royals to win the world series at 30/1. Sportsbooks didn’t want to take all his money so he spread it across 15 different casinos and his hard work paid off. The Royals ended up winning the world series and Vegas Dave brought home $2.5 million dollars.

3. 15-Leg NFL Parlay

Parlays are always tough but sometimes the payouts are too good to pass up. Tayla Polia decided to take a chance on a 15-leg parlay in the NFL that paid out 20,000/1 and it has been reported that this was only her 2nd ever bet. Her parlay featured 9 favorites, 5 underdogs, and 1 over/under. Even though there was only $5 placed on this wager it ended up hitting and she took home $105,000 for her troubles. It is unclear how many times a 15-leg parlay has been hit, but we are willing to bet it can be counted on less than two hands.

4. Leicester City Premier League Future 

Leicester City winning the Premier League in 2015 was one of the biggest upset wins in this history of sports. Before the season had started they were 5000/1 underdogs but someone was willing to take a shot on them to win it all. A bettor placed a wager of £100 and walked away with £200,000. Not only is the bet crazy but the fact that Leicester City was able to take down some of the biggest in England is a story of its own.

5. “Vegas Dave” Holly Holm vs Ronda Rousey

The Kansas City Royals future bet wasn’t the only big-time win Vegas Dave has had. When Ronda Rousey was at her top in the UFC nobody thought she could be beaten, until it happened. Rousey took on Holly Holm in the main event of UFC 193 and Holm came into the fight as an 11/1 underdog. Dave ended up placing a $20,000 wager on Holm to win and she did just that, netting Vegas Dave $200,000 in the process. Say what you want about Vegas Dave now, but you can’t deny he has had some big wins in the past. Just maybe don’t pay for his picks that he sells on social media.

6. Phil Mickelson Baltimore Ravens Future

Phil Mickelson is known by the world as one of the best golfers of all-time, but he is also known to be an avid gambler as well. This was true before the 2000/2001 NFL season when Mickelson decided to place a $20,000 wager on the Baltimore Ravens to win the Super Bowl at 22/1 odds. The Ravens went on to defeat the New York Giants and the win netted Mickelson $560,000 dollars. Phil doesn’t need the money so we assume that funded more of his betting in the years closely following. 

7. Billy Walters New Orleans Saints $3.5 Million Bet

Walters ran into some trouble with the law in recent years due to insider trading, but prior to that, he was known as one of the best sports bettors in the business. In 2010 with the New Orleans Saints set to take on the Indianapolis Colts, Walters placed a $3.5 million dollar wager on the underdog Saints. New Orleans ended up surprising the Colts and took home the 31-17 victory in Super Bowl XLIV. Walters has claimed in the past to make between $50-$60 million while sports betting in a “good year”. He was sentenced to 5 years in prison in 2017 but due to the COVID-19 pandemic, he was released to home confinement in 2020. It is unclear if he continues to bet on sports.

8. Charles Barkley $800,000 Patriots Super Bowl

Charles Barkley is a lot like Phil Mickelson, he is widely known for his success in his sport but they are popular amongst others for their gambling habits. Barkley talks a lot about his losses and wins but one of his biggest wins came when he placed $500,000 on the New England Patriots to win the Super Bowl in 2002. They were 14 point underdogs vs the Rams but that didn’t scare Barkley away and he cashed out and walked away with $800,000. However, further down the line, Barkley placed a 100k wager on the Falcons to beat the Patriots in the Super Bowl and he had to watch them blow a 28-3 lead and his 100k go by the wayside.

9. Richard Hopkins Lewis Hamilton Futures

Richard Hopkins discovered Lewis Hamilton when he took his own son to a go-kart track in 1998. Hopkins then decided to place a £200 wager that Hamilton would win a Grand Prix by the young age of 23 with 300/1 odds. He also did the same for him to become a world champion at 500/1 odds. These both ended up happening and Lewis Hamilton is now known as one of the greatest Formula 1 drivers of all time. With these bets, Richard Hopkins came away with £165,000

10. 5-Leg NFL Parlay for $250,000

In 2017 an MGM bettor in Las Vegas decided to put down a wager on a  5-leg parlay that featured 4 favorites (Ravens, Patriots, Chiefs, and Raiders) and concluded with the Detroit Lions. Unlike the previous parlay, there was quite a bit of money placed on this one, $8,500, but the payout was huge. With the Lions securing the parlay win with a 24-10 victory over the Giants the bettor walked away with $250,000. This went down as one of the biggest parlays wins in the sports betting space.

  
Tyler currently runs the lineups.com twitter handle, posting various content including betting trends, player trends, and game previews. Tyler is the Lineups.com Swiss army knife, managing our social media as well as research and writing.

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