Betting on sports has created some of the most unbelievable wins in history, with lucky gamblers turning tiny wagers into life-changing fortunes. From football upsets to horse racing miracles, these betting stories prove that sometimes, against all odds, dreams do come true.
Here’s a countdown of the 25 biggest and most memorable sports betting wins ever recorded!
25. Adrian Hayward – £25,000 on a £200 Bet
In 2005, Liverpool fan Adrian Hayward bet £200 that Xabi Alonso would score from his own half in an FA Cup match. When Alonso’s stunning long-range goal found the net in 2006, Hayward cashed out £25,000 at 125-1 odds.
24. Anonymous Punters – $76,000 on a $0.10 Bet
Two horse racing bettors in Saratoga Springs, USA, hit the jackpot with a superfecta wager, predicting the top four horses in exact order at 88/1 odds. Their $0.10 bet earned them a whopping $76,000 (£58,000).
23. Tayla Polia – $105,000 on a $5 Bet
With only one previous bet in her life, Tayla Polia placed a 15-leg NFL parlay. Against 20,000-to-1 odds, she won $105,000 (£80,000) from her $5 wager, proving that beginner’s luck can be real!
22. Gerry McIlroy – £100,000 on a £200 Bet
In 2004, Gerry McIlroy bet £200 that his 15-year-old son Rory would win the British Open within 10 years at 500-1 odds. When Rory McIlroy claimed victory over Sergio Garcia and Rickie Fowler, his proud father pocketed £100,000.
21. Nicholas Newlife – £101,840 on a £1,520 Bet
British bettor Nicholas Newlife predicted Roger Federer’s Wimbledon dominance in 1999. He placed £1,520 on Federer winning six or more Wimbledon titles. When Federer secured his sixth title in 2009, Newlife’s estate collected £101,840—as he had passed away before seeing his win.
20. Peter Edwards – £125,000 on a £50 Bet
In 1996, Peter Edwards bet £50 that his grandson, Harry Wilson, would play for Wales’ national football team. Wilson’s international debut in 2013 won his grandfather £125,000—at just 16 years old!
19. Mick Gibbs – £157,000 on a £2.50 Bet
In 1999, roofer Mick Gibbs placed a £2.50 accumulator bet on nine football games across Europe. Every result came through, earning him £157,000—but this was only the start of his luck.
18. Richard Hopkins – £165,000 on Several Bets
In 1998, Richard Hopkins bet £200 that a young Lewis Hamilton would win a Formula 1 Grand Prix before 23 and a World Championship before 25. In 2008, Hamilton’s first F1 title landed Hopkins a £165,000 payout.
17. Vegas Dave – $200,000 on a $20,000 Bet
Famous gambler Dave Oancea (Vegas Dave) bet $20,000 on Holly Holm beating Ronda Rousey in UFC 193. Holm’s shocking underdog victory earned him a massive $200,000 (£150,000).
16. Anonymous Punter – $250,000 on an $8,500 Bet
In 2017, a mystery bettor at MGM Resorts placed an $8,500 parlay bet, correctly predicting five NFL results. His bet returned $250,000 (£191,000)—one of the biggest wins that season.
15. Anonymous Punter – £200,000 on a £100 Bet
A bold Leicester City fan bet £100 at 5000/1 odds on them winning the 2015 Premier League title. Against all odds, Leicester lifted the trophy, securing him £200,000.
14. Anonymous Punter – $305,375 on a $5 Bet
A Las Vegas bettor placed a $5 parlay on 12 basketball games, including NBA matchups. Against incredible odds, they won $305,375 (£233,000).
13. Erick Lindgren – $340,000 on a Side Bet
Poker pro Erick Lindgren took a high-stakes bet that he could play four rounds of golf in Las Vegas, scoring under 100 each time. Against expectations, he pulled it off and won $340,000 (£259,000).
12. Anonymous Punter – $375,000 on a $500 Bet
A Las Vegas gambler bet $250 on the St. Louis Cardinals winning the NL pennant and another $250 on them winning the World Series. His winnings? $375,000 (£286,000).
11. Phil Mickelson – $560,000 on a $20,000 Bet
Golf legend Phil Mickelson bet $20,000 on the Baltimore Ravens to win Super Bowl XXXV (2000)—pocketing $560,000 (£426,000).
10. Mick Gibbs – £500,000 on a £0.30 Bet
Roofer Mick Gibbs struck gold again in 2001, winning £500,000 on a £0.30 bet with a 15-leg accumulator.
9. Darren Yates – £550,000 on a £62 Bet
In 1996, Darren Yates bet £62 that jockey Frankie Dettori would win all seven races at Ascot. Dettori did, earning £550,000.
8. Anonymous Punter – £585,000 on an £0.80 Bet
A William Hill customer won £585,000 from an 80p bet on 19 football matches in 2011.
7. Charles Barkley – $800,000 on a $500,000 Bet
NBA star Charles Barkley bet $500,000 on the New England Patriots to win the 2002 Super Bowl, winning $800,000 (£608,000).
6. James Adducci – $1.2 Million on an $85,000 Bet
James Adducci bet $85,000 on Tiger Woods winning the 2019 Masters, earning $1.2 million (£760,000).
5. Mike Futter – £800,000 on His Own Horse
Mike Futter bet on his own horse, Monty’s Pass, to win the Grand National, collecting £800,000.
4. Fred Craggs – £1 Million on a £0.50 Bet
Fred Craggs placed a £0.50 accumulator bet in 2008, winning £1 million.
3. Steve Whiteley – £1.5 Million on a £2 Bet
Steve Whiteley won £1.5 million from a £2 bet on six horse races in 2011.
2. Vegas Dave – $2.5 Million on a $140,000 Bet
Vegas Dave bet $140,000 on the Kansas City Royals winning the 2015 World Series, winning $2.5 million (£1.9m).
1. Billy Walters – $3.5 Million on a Super Bowl Bet
Billy Walters placed a $3.5 million bet on the New Orleans Saints winning Super Bowl XLIV (2010), netting a record-breaking win of $3.5 million (£2.7m).
Final Thoughts
From pennies to millions, these betting wins prove that anything is possible—if you beat the odds!
