10 Biggest Bets Ever Won in History

Betting on sports and gambling has been around for centuries, and over time, there have been moments when punters made history by beating the odds. Sometimes, it was seasoned gamblers spotting great odds where others didn't, while even beginners made it to our list of biggest bets ever won in history.

During our research, we found out that some betting wins are well-documented, but some were difficult to verify. In this article, we're looking at ten of the biggest-ever betting wins we could confirm. There could be more out there, but many large-scale wins go unreported since most look to remain anonymous. Here are the 10 best bets that were even won.

• Initial Bet: £50 bet in 2000 at odds of 2,500-1 that Harry Wilson would play for Wales

• Amount Won: £125,000

In 2000, Peter Edwards placed a £50 bet at odds of 2,500-1 that his toddler grandson would one day join Wales' national football team. The toddler in question was Harry Wilson, and his chances of someday representing his country were unknown. However, Wilson made his international debut for Wales at 16. He netted his grandfather one of history's most heartwarming bets ever won.

This win allowed Edwards to retire a year earlier than he planned.

• Initial Bet: $20,000 (approx. £15,000)

• Amount Won: $560,000 (approx. £420,000)

Phil Mickelson has earned millions playing golf. However, the golfer also won a couple of substantial bets throughout his career, the most notable one dating back to the early 2000s. Mickelson placed a $20,000 (or approx. £15,000) bet on the Baltimore Ravens to win the NFL Super Bowl. The odds of this happening were 22/1, as the Ravens were the underdog team.

However, the Ravens ended up crushing their opponents in this final in a 34-7 victory, allowing Mickelson to take home $560,000 (or approx. £420,000.)

The most impressive part of Mickelson's bet was that it didn't rely on an accumulator. It was a risky and statistically unlikely bet, which netted a substantial payout when the unexpected happened.

• Initial Bet: £2.50 in 1999, £0.30 in 2001

• Amount Won: £157,000 in 1999, £500,000 in 2001

Mick Gibbs was a roofer from Staffordshire who became a legendary name in the betting world after winning amazing accumulator bets. In 1999, Gibbs placed a £2.50 accumulator bet to predict the outcomes of nine football games. This acca earned him £157,000, which was only the beginning for him. In 2001, Gibbs broke his record with a £500,000 win following a 15-fold accumulator with a 30p wager.

Gibbs is an impressive story for us since accumulators are often advised against punters looking to beat the betting apps, but the feature still netted Gibbs one of the biggest bet ever won in football. However, Gibbs managed to beat the odds 1.6 million to one with his 2001 win, which showcases why Accas will always remain popular despite their mission impossible-like odds of happening.

• Initial Bet: Approx. $18,000 (or £14,000)

• Amount Won: $200,000 (or £150,000)

Dave Oancea, or Vegas Dave, has a long history of scoring big wins in his betting career. While Oancea has won millions through sports betting, his most influential win was when he betted on Holly Holm to deaf Ronda Rousey at UFC 193. Rousey was undefeated at the time, and she was arguably the favourite in the match-up. Oancea took the 11-to-1 odds and backed Holly Holm, who ended up winning and took home $200,000 (or £150,000.)

In the same year as UFC 193, 2015, Oancea won $2.5 million (or £1.9 million) when he betted on the Kansas City Royals to win the World Series. He also followed this futures bet with another in 2016 when he won another $2.3 million (or £1.7 million) after the Denver Broncos won Super Bowl 50.

• Initial Bet: $550,000

• Amount Won: $800,000

NBA legend Charles Barkley isn't a stranger to taking calculated risks. In 2002, Barkley bet $550,000 (or £410,000) on the New England Patriots. Their opponents, St. Louis Rams, were heavily favoured to win, and the match itself was pretty close. However, all worked out in Barkley's favour, and he won $800,000 (or £600,000.)

Barkley's win also marked Tom Brady's first-ever Super Bowl ring. Considering Barkley's initial stake was relatively higher than some of the other entries on our list, it makes his bet one of the riskiest based on numbers.

• Initial Bet: £2

• Amount Won: £1.4 million

Steve Whiteley is a heating engineer who hit the jackpot during a free day at the Exeter Racecourse. Whiteley placed a Tote Jackpot bet with £2, where he chose a winner for each of the six races. These picks were based on the names of the horses, as one of Whiteley's choices hadn't won a single race in 28 appearances, while another horse happened to win for the first time ever. With a bit of luck, however, Whiteley took £1.4 million, which isn't too bad for a day's work at the racks.

According to Whiteley, he liked horse racing, but he knew nothing about horses. Considering he almost didn't even place a bet, this is a memorable underdog win.

• Initial Bet: £0.50

• Amount Won: £1,000,000

Fred Craggs decided to bet on an eight-fold accumulator with odds of 2 million to 1 during his birthday in 2008. As he was going about his day, the horses he chose suddenly started pulling through. First, the horse "Isn't That Lucky" started the chain of events, and the final horse, "A Dream Come True," sealed the deal. Cragg's £0.50 bet turned into £1 million, but he only realised this was the case when he returned to his local William Hill shop.

This was an inspiring occasion as it highlighted the random and beautiful nature of betting.

• Initial Bet: $85,000 (or £63,000)

• Amount Won: $1,200,000 (£900,000)

James Adducci's story is an odd one. The US-based punter had little to no history in sports betting before he flew to Las Vegas with $85,000 (or £63,000) to place a futures bet on Tiger Woods to win the Master tournaments. Considering Woods had been cold for 11 years, the odds for him were 14-to-1. This risky move paid off as Woods performed extremely well in the tournament and earned Adducci $1.2 million (or £900,000.)

Following this win, Adducci placed a new bet, $100,000 (or £75,000) on Woods to win all four majors that year. Though this bet didn't pay off, it would net Adducci close to $10 million (or £7.5 million) if it were to play out.

• Initial Bet: Unknown

• Amount Won: $3.5 million (or £2.6 million)

Billy Walters is a successful punter with a long history in the betting world. During the 2010 Super Bowl, Walters took home $3.5 million (or £2.6 million.) He bet on the underdogs, the New Orleans Saints to beat the Indianapolis Colts, and the outcome Walters hoped for happened with a score of 31-17.

Unlike some candidates on our list, Walters could be considered an experienced bettor. He improved his methods throughout the years, using advanced analytics and statistics to make educated decisions in his path to outsmart the odds.

• Initial Bet: $10 million (or £7.5 million)

• Amount Won: $75 million (or £56 million)

Another experienced punter, Jim "Mattress Mack" McIngvale is topping our list. The businessman made betting history in 2022 when he placed a $10 million (or £7.5 million) bet on the Houston Astros to win the World Series. This nail-bitingly high stake netted McIngvale $75 million (or £56 million) as the Astros won the title at the end of that year. This is believed to be the largest payout in American sports betting history, with his biggest payout coming from the Caesars Sportsbook at $30 million alone.

Interestingly enough, McIngvale strategically uses betting apps and sportsbooks to hedge promotions at his furniture store strategically. During the year when he won the bet, customers who spent $3,000 (or £2,200) at his store were eligible to double their money back if the Astros won. A part of McIngvale's winnings fueled these refunds, but he should still have plenty of leftovers.