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Biggest Parlay Bet Wins in History | Infographic

Parlay bets are among the riskiest and most rewarding bets anyone can make, even with only a low stake. Several people have already won big because of parlays even after staking only a few pence on a bet.

Most sports bettors place 1X2, over/under, and BTTS bets and group them up for parlays to have higher odds than the low odds those markets usually have. Other big parlay winners also won big through horse races. What these people have in common is that they all got extremely lucky that all their bets won or only one of their bets ended in a loss, still allowing them to win big.

The biggest parlay winners we’ve listed below are those who won millions or at least several hundred thousand out of a few dollars, not exceeding $100. Some of these have already been featured in our previous article on the biggest sports betting wins in history since they’re also the ones who’ll likely win big in sports betting. Any sports bettor who wants to try and replicate these wins can do so by SG horse betting and sportsbook betting in Singapore.

Biggest Parlay Bet Wins in History

Steve Whiteley - £1,445,671.71

The biggest parlay win ever in horse racing is that of Steve Whiteley, who won a horse racing parlay in March 2011. He was a heating engineer in North Tawton who visited an Exeter racecourse and bet on the Tote Jackpot thanks to a free promotion.

The goal of the Tote Jackpot was to predict six winners on a card to win the jackpot, and Whiteley placed six bets at random, namely the following:

  • Semi Colon (2-1)
  • Black Phantom (12-1)
  • Ammunition (16-1)
  • Mr Bennet (16-1)
  • Lundy Sky (5-1)
  • Lupita (12-1)

Keep in mind that Lupita had not won a single race in its last 26 races at the time and its jockey, Jessica Lodge, had no prior wins. In the end, Whiteley’s predictions were correct, and he won £1,445,671.71.

Fred Craggs - $1,258,288

Before Steve Whiteley, another horse racing bettor also won big through a parlay. Fred Craggs was a fertilizer salesperson from Thirsk, New Yorkshire, who frequently placed small bets as a hobby. In February of 2008, he placed a small 50p eight-horse parlay bet and won £1 million or $1,258,288 while also becoming 2008’s biggest horse racing winner.

Craggs got lucky when he followed his instinct on placing the parlay bet as he won millions from the 50 pence bet on a parlay with 2,000,000/1 odds. This win was also the largest parlay payout in his life.

BetMGM Bettor - $1,133,530

One bettor won a ridiculous amount of money by hitting a ridiculous 15-leg parlay with total odds of +22670. This BetMGM bettor won $1,133,530 from a $50 bet on a parlay filled with nearly the entire sports spectrum. The bettor’s parlay featured eight college teams, three NHL teams, two NFL teams, one NBA team, and one golfer. The bettor managed to hit every single leg of the parlay, even those with high odds. Every leg of the parlay included the following:

  • Vegas Golden Knights +2.5 (-105)
  • Cal State Fullerton ML (-150)
  • Rhode Island -5.5 (-110)
  • UConn -24.5 (-110)
  • Miami Ohio -9.5. (-110)
  • Wake Forest -9.5 (-110)
  • Michigan State -2.5 (-110)
  • Atlanta Hawks ML (-190)
  • Colorado Avalanche -1.5 (+150)
  • Washington Capitals -1.5 (+200)
  • New England Patriots ML (-275)
  • Houston ML (-300)
  • Oklahoma ML (-175)
  • Jin Young Ko (+500)
  • Baltimore Ravens ML (-250)

Some of the interesting legs of the parlay were the Ravens moneyline bet and the Jin Young Ko bet to win the CME Group Tour Championship. The Young Ko bet was undoubtedly the most difficult leg to predict since golf tournament winners are tough to predict.

Anonymous Bettor - $966,290

The 2021 Ryder Cup was a disaster for the Americans as they easily dismissed their European competitors. One sports bettor still risked placing a 12-leg parlay that went down in history as one of the most impressive parlay bets ever. Out of the 12 legs, six were favourites, four were underdogs, and two were ties. Picking these specific outcomes won’t likely result in a win, but one bettor who picked these managed to turn their $8 to $966,290. The legs included the following:

  • Koepka (-154)
  • DeChambeau (-105)
  • Tie between Morikawa vs Hovland (+550)
  • Berger (-173)
  • Johnson (-159)
  • Westwood (+190)
  • Tie between Spieth vs Fleetwood (+650)
  • Thomas (-159)
  • Cantlay (-120)
  • Scheffler (+230)
  • Poulter (+200)

Mcllroy (+180)


It’s possible to get lucky and win big through parlays, and people should try placing parlay bets more from time to time, especially when they’re only staking low. Some of the biggest wins didn’t involve betting thousands of dollars to win big since some people spent only a few pence to win big through sheer luck.

Sports bettors only need to look for a reputable sports betting site to start betting on the following sportsbooks:

One betting site and online casino that both Singaporean and Malaysian bettors can bet on is CM2Bet. Bettors can enjoy football betting in Malaysia and Singapore through CM2Bet without worrying about getting scammed off their winnings. Register today and start betting with us.

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