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Biggest Sports Betting Wins in History ( Infographics )

Sports betting is exciting because it allows sports fans to support their favourite teams while potentially winning some money. Many people might think that sports betting wins only amount to a few hundred dollars at most, but there have already been several big wins in sports betting in recent history.

Simple moneyline bets and relatively simple goal-based wagers like the both teams to score and odd/even market is not enough to generate large profits. Bettors will either have to look for bookmakers offering jackpots, bet on parlays of simple bets, or use the outright betting market. Some bettors also had to make multiple bets on different casinos and sportsbooks to take advantage of the different odds offered on a single match to make more money.

We’ll talk about some of the biggest wins while keeping the stakes in mind. Not everyone can go around staking hundreds of thousands of dollars to make millions, AND IT IS POSSIBLE to win hundreds of thousands to millions of dollars with only some spare change.

Biggest Sports Betting Wins in History

Anonymous Bettor - $14 Million

One lucky bettor won $14 million after winning a successful bet between the L.A. Dodgers and the Houston Astros during the 2017 World Series. The mysterious bettor placed multiple bets on different bookmakers in Las Vegas and let the whole thing ride for up to six games. He made the mammoth $14 million win after game six on November 1, 2017.

Steve Whiteley - £1.45 Million

A 61-year-old heating engineer, Steve Whiteley, placed a mere £2 or $2 bet from a free horse racing ticket and ended up with a whopping £1.45 million or about $1,825,274 million in 2011. He managed to match six horses on the Exeter Tote or Pari-mutuel Jackpot, where one of the horses he selected lost its last 28 races. Arguably, no one in their right mind will bet on a horse that has already lost multiple races.

Steve didn’t have any strategy when picking horses and picked them seemingly randomly.

Fred Craggs - $1,258,288

Fred Craggs, a 60-year-old fertiliser salesman, ended up becoming a millionaire after staking a mere 50p on an eight-leg parlay consisting of different horse races worldwide. He only realised that he had won £1 million or approximately $1,258,288 million when he returned to his local bookmaker to place another bet.

Anonymous Leicestershire Bettor - $1,035,585

In the U.K., one more mysterious bettor from Leicestershire took home £823,000 or about $1,035,585 from a mere £19 five-leg horse racing parlay bet. The bettor won it on a horse racing meet in April 2017.

Anonymous Malta Bettor - $735,783

Another anonymous bettor from Malta placed a small $1 bet and profited £585,000 or approximately $735,783. The punter used a 19-fold accumulator with odds of +68373800. Liverpool’s winning goal in the last three minutes of its match against Chelsea secured the bettor’s six-figure payout.

Darren Yates - $693,296

A big name in the horse racing betting scene, Darren Yates managed to successfully place a £62 wager on the jockey Frankie Dettori to win all seven rides on the Magic Seven at Ascot in September 1996. Dettori’s win then resulted in Yates’s win of £550,823 or $693,296.

Mick Gibbs - $629,237

A measly £0.30 bet can end up to £500,000 or approximately $629,237 through a 15-leg accumulator with a total of +166666600 odds. Mick Gibbs, an English roofer, made this bet and 14 of his predictions came out correctly, with the last match ending in penalties.

Anonymous Las Vegas Bettor - $305,375

A lucky Las Vegas bettor managed to turn a small $5 parlay to $305,375. The lucky gambler wagered on professional and college basketball games and correctly guessed the 12 winners of those basketball matches.

Tayla Polia - $105,000

Tayla was only a beginner in the betting scene when she won $105,000 only on her second bet. She staked a $5 bet on a 15-leg parlay in the NFL, which paid out around a hundred thousand dollars. The parlay featured nine favourites, five underdogs, and one over/under bet. A parlay is already hard enough, and winning a 15-leg one only on their second bet is impressive and incredibly lucky.


Winning big through sports betting is indeed possible. Still, bettors will have to either get lucky or research deeply to predict the outcome of multiple matches for a parlay accurately. Some bettors grind and place numerous bets across different sportsbooks to take advantage of their different odds and maximise their winnings.

Singaporean and Malaysian sports bettors can replicate the successes mentioned above by continuously placing bets and learning more of the matches they’re betting on. Who knows, they can also get lucky when placing the occasional parlay or jackpot bets. Singaporeans will only need to look for a reputable traditional or online casino in Singapore, while Malaysians need to look for a licensed traditional casino or a trusted online casino in Malaysia. This way, no bettor will get scammed off their winnings when they finally make millions.

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