Betting | Mar 14, 2023

Biggest sports betting wins

By Ezra

Biggest sports betting wins twit

In the history of legal sports betting, only a few have been lucky enough to win extraordinarily big. Below are some of the 8 biggest sports betting wins of all time across Major League Baseball (MLB), horse racing, golf, National Football League (NFL), and English Premier League (EPL).

Major League Baseball (MLB)

Dave Oancea - $2.5 million

Dave Oancea from Las Vegas, also known as ‘Vegas Dave’, won an enormous $2.5 million on a bet worth $140,000 in 2015.

Oancea placed the bet on the Kansas City Royals winning the World Series championship at 30/1 odds, wagering it across 15 different sportsbook casinos. Earlier that same month, Oancea also won $200,000 from a $20,000 bet on Holly Holm beating Ronda Rousey in the UFC 193 so sportsbooks saw his bet as a liability.

These two incredible big betting wins have earned Oancea a place in sports betting history!

Horse Racing

Steve Whiteley - £1.45 million (approx. $1,766,612)

Steve Whiteley, a 61 year old heating engineer, won £1.45 million on a free £2 accumulator bet, back in 2011.

Whiteley bet a six-fold parlay on horses Mr. Bennett (16/1), Ammunition (16/1), Semicolon (2/1), Black Phantom (12/1), Lupita (12/1), and Lundy Sky (5/1) to win at the Exeter Tote Jackpot. What made his win even more incredible was the fact that Lupita’s jockey, Jessica Lodge, had never won a race in her 28 attempts!

Pexels photo 1462361

Darren Yates - £550,000 (approx. $670,073)

In 1996, Darren Yates won £550,000 on a £62 bet wager.

Yates placed the bet on his favourite Italian jockey, Frankie Dettori, winning all seven of his races at the Royal Ascot. Some of the multiple accas had huge odds against them of 25,000/1!

Dettori’s near-impossible winning streak went down in horse racing history that day.


James Adducci - $1.2 million

Back in 2019, James Adducci won an outstanding $1.2 million on a $85,000 wager.

Adducci placed the bet on Tiger Woods winning the Masters Tournament at the William Hill sportsbook at 14/1 odds. It was a risky move for Adducci, considering at that time Woods had not won a championship in a long time. That day, he broke William Hill’s record for the largest individual payout on a futures bet.

Pexels photo 114972

National Football League (NFL)

Charles Barkley – $800,000

Former professional basketball player Charles Barkley won $800,000 on a $500,000 bet in 2002.

Barkley placed the bet on the New England Patriots winning the Super Bowl XXXVI. The Patriots were highly unlikely to win that year, being the 14-point underdog against the St. Louis Rams.

Phil Mickelson - $560,000

In 2000, professional golfer Phil Mickelson won $560,000 on a $20,000 bet.

Mickelson placed the bet on the Baltimore Ravens winning the Super Bowl XXXV at 22/1 odds, way before the season began.

Tayla Polia - $105,000

In 2015, Tayla Polia won $105,000 on a $5 bet.

Polia placed a 15-leg NFL parlay that consisted of five underdogs on the moneyline, nine favourites, and one over/under. The bet was a longshot with 20,000/1 odds.

In full, Polia’s bet was: Minnesota Vikings -5, Atlanta Falcons +3, Houston Texans +1, Kansas City Chiefs -8, Washington Redskins +1, New England Patriots -14, Arizona Cardinals -4, New York Giants +5, Seattle Seahawks -14, Green Bay Packers -3, Los Angeles Chargers -2, Pittsburgh Steelers -6, Pittsburgh Steelers / Denver Broncos over 45, Cincinnati Bengals -4, and Detroit Lions +3.

English Premier League (EPL)

Unknown - £200,000 (approx. $243,663)

In 2015, an unknown bettor won £200,000 on a £100 bet.

The bet was placed on Leicester City winning the English Premier League, being the underdogs with 5000/1 odds against them before the start of the season.

Unknown - £585,000 (approx. $711,401)

Back in 2011, an unknown bettor won £585,000 from an 80p bet.

The bet was a 19-match accumulator, placed on William Hill, with seemingly impossible odds of 683,738/1. When Liverpool beat Chelsea in the final 3 minutes of the match, the better secured the six-figure payout.