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Biggest Winning Bets Ever

From being considered a hush-hush activity to some of the world’s best cricket betting sites increasingly catering to Indians today, online betting in the country has undoubtedly come a long way. Its popularity is, to a large degree, courtesy of the ease with which punters can bet on sports like cricket, football, kabaddi, horse racing, and the like.

That said, let’s now take a look at the 10 biggest sports winning bets of all time.

Biggest Sports Betting Wins In History

We shall cover these top-down, starting from the biggest winning bets.

*All winnings converted to INR as per prevailing forex rates on January 9, 2022

1. New Orleans Saints Super Bowl Bet

  • Bet by: Billy Walters
  • Wager amount: $3.5 million
  • Winnings: Unknown

Billy Walters, a popular poker player and a familiar face at some of the best online lotteries, ventured into sports betting and made a splash almost instantly. He put down a whopping $3.5 million on a single bet on the New Orleans Saints during the Super Bowl XLIV. New Orleans Saints, considered by most the underdogs that season, registered a famous victory over Indianapolis Colts, winning their first-ever Super Bowl with a 31-17 scoreline.

While we don’t know yet how much Walters won from his wager, it definitely must have been an enormous windfall. Surely one of the biggest sports betting wins of all time.

2. Kansas City Royals Futures Bet

  • Bet by: Dave Oancea
  • Wager amount: Somewhere between $1,00,000 and $1,40,000
  • Winnings: $2.5 million (₹18,56,93,750)
  • Approx. returns: 2,400%

This Las Vegas gambler, who goes by the moniker of ‘Vegas Dave’, clearly has a penchant for picking some BIG winners. In 2015, Dave put his greenbacks on Kansas City Royals to win the World Series (baseball) at odds of 30.00. Due to the risky nature of his bet, Dave had to spread it across 15 bookmakers, as none were ready to shoulder that massive a liability alone.

The result? Kansas City Royals won the 2015 World Series, and Dave his thumping $2.5 million.

3. Exeter Tote Jackpot (Acca)

  • Bet by: Steve Whiteley
  • Wager amount: £2
  • Winnings: £1.45 million (₹14,63,51,264)

What a turnaround year 2011 was for 61-year-old Steve Whiteley. With a modest £2 stake (from a free horse racing ticket), the heating engineer amassed an astronomical £1.45 million. Whiteley correctly predicted as many as six winning horses on the Exeter Tote Jackpot. What was more surprising is that one of those selections was on a 28-race losing spree at that time!

Steve Whiteley’s 6-horse accumulator consisted of Semicolon, Black Phantom, Mr. Bennett, Lundy Sky, Lupita, and Ammunition, all taking part in races across the UK and Ireland.

4. Eight-Fold Horse Racing Acca

  • Bet by: Fred Craggs
  • Wager amount: 50p
  • Winnings: £1 million (₹10,09,31,906)

Sample this. You bet ₹50 on a horse racing accumulator, hoping to win a handful. By a stroke of luck, that “handful” becomes ₹10 crores, and you walk home a crorepati!

That’s precisely what happened with 60-year-old Fred Craggs. The fertiliser salesman probably had the best day of his life when he amassed £1 million with a meagre 50p stake on an eight-fold horse race betting acca. It was only when the Yorkshireman went to place another wager at the same bookie that he realised the fortune he had come into.

5. Tiger Woods Masters Bet

  • Bet by: James Adducci
  • Wager amount: $85,000
  • Winnings: $1.2 million (₹8,91,33,000)
  • Returns: 1,312%

At one point, the demons of Tiger’s personal life started spilling over to the tabloids, landing a telling blow to the famed golfer’s game, with pundits beginning to write him off for good. So when James Adducci wagered $85,000 on Woods to win the 2019 Masters Tournament, not many would’ve really given him a chance.

But the bettor remained unfazed, and what was a risky move ended up being extremely rewarding. Adducci won $1.2 million on his futures bet with William Hill, registering a staggering 1,312% of his stake. The best part? It was Adducci’s first-ever sports wager.

6. Monty’s Pass 2003 Horse Racing Bet

  • Bet by: Mike Futter
  • Wager amount: Unknown
  • Winnings: £8,00,000 (₹8,06,22,549.28)

Belfast-based Mike Futter’s enormous win from a bet on his own horse headlined news stories back in the day. In 2003, the gambler, known for owning 11 bingo halls, bet on Monty’s Pass and sent the cash registers ringing with winnings worth £348,000 (for being the owner of the horse) and then a massive £400,000 for his successful wager.

7. Darren Yates’ Magnificent Seven

  • Bet by: Darren Yates
  • Wager amount: £62
  • Winnings: £5,50,823 (₹5,54,75,413.01)
  • Approx. returns: 8,88,324%

In 1996, Darren Yates bet £62 with William Hill on jockey Frankie Dettori to ride seven winners at Ascot. In return, Yates took home an astronomical £5,50,823 in what he described years later as “the best moment of my life”. The 55-year old used the fortune to build his property and establish an empire, which he sold later at £20 million.

He said, “I'd been playing football for my local team in Morecambe and only caught the racing results over a post-game pint. I asked how it was going, and they said Dettori had four out of four. I reckoned I'd won £700. Then Frankie's fifth and sixth horses went in, and I thought I was heading for the £24,000 mark. So I went down to the betting shop to watch the seventh race and just quietly sat there. I couldn't believe it when Frankie stormed home.

“I asked the counter girl how much I'd won, thinking it would be about £50,000. When she told me it was over £500,000 I almost fainted. I went home and just burst out crying.”

Going by the returns, this ranks right up there with some of the biggest sports betting wins in history.

8. Baltimore Ravens Superbowl Futures Bet

  • Bet by: Phil Mickelson
  • Wager amount: $20,000
  • Winnings: $5,60,000 (₹4,15,95,400)
  • Returns: 2,700%

Golfer Phil Mickelson had a hunch that Baltimore Ravens would win the 2001 Super Bowl, and he decided to make good of it, forming a syndicate and putting down a futures bet on the American football team at odds of 22.00. As luck would have it, the Ravens won the NFL championship game, and Phil his $560,000.

Considering the golfer’s appetite for gambling, we’re not sure if this would’ve been his biggest scoop, but it still is one of the biggest sports betting wins in recorded history.

9. Leicester City EPL Futures Bet

  • Bet by: Anonymous
  • Wager amount: £100
  • Winnings: £2,00,000 (₹2,01,86,381)
  • Approx. returns: 1,99,900%

Leicester City winning the English Premier League in 2015 was one of the most exemplary and inspirational stories of the underdogs soaring above the rest, a moment that will probably never be forgotten. While the victory sent shockwaves across the international footballing scene, one anonymous punter somewhere around the world was smiling from ear to ear after netting a whopping £200,000 with a £100 stake.

10. 15-Leg NFL Parlay

  • Bet by: Tayla Polia
  • Wager amount: $5
  • Winnings: $1,05,000 (₹77,99,137)
  • Returns: 20,99,900%

Think the above figure is a typo? It's not. It is just $5 that won Tayla Polia a bumper $105,000 on a 15-leg NFL parlay.

For the uninitiated, a parlay is a cumulative series of wagers, where winnings from each bet become the stake for the next bet. It pays out only if you win all the bets. As you can fathom, it is difficult to win a 3- or even a 2-bet parlay. But luck was on Tayla’s side as she won a near-improbable 15-leg parlay at odds of 20,000.00!

The craziest part? It was her second-ever wager, and what a bet to have come through!

Biggest Sports Betting Wins FAQs

What is the maximum payout limit at bet365?

With bet365, the maximum winnings in any given 24-hour period varies across sports and competitions. The highest payout limit is £2,000,000, applicable to football. This is limited to men’s international competitions, including the EPL, League1, League 2, EFL Championship, La Liga, Bundesliga, Serie A, FA Cup, UEFA Champions League, UEFA Europa League, and French Ligue 1.

All winnings are exclusive of stake.

What is the maximum payout limit at Betway?

The maximum limit differs across sports. The highest winnings are capped at £5,00,000, applicable for international footballing competitions, including EPL, Champions League, Bundesliga, and La Liga.

What is the maximum payout limit at Parimatch?

At Parimatch, the highest winnings from one bet are the equivalent of $1,000,000 (as per the gaming account currency).

What is the maximum payout limit at 1xBet?

At 1xBet, the maximum winnings per bet are capped at €600,000 (or the equivalent of foreign currency).

What is the maximum payout limit at 10CRIC?

The maximum total winnings in any 24-hour period across all 10CRIC products are €50,000 (or the equivalent of gaming account currency).

Is there a particular strategy one must follow to register the biggest sports betting wins?

There’s no single strategy, really. It depends on the sport you bet on and your wagering requirements – and, of course, a generous dose of luck.

For example, matched betting ensures guaranteed winnings at zero risk to your stake. You can check out our no-risk matched betting guide, where we have covered it in detail.

That said, the most vital strategy, if there were one, to registering the biggest sports betting wins is understanding the sport, finding favourable odds, and more importantly, not going overboard.

CricketBettingAdvice Final Say

Sports betting can be very rewarding if things go your way, but only when you test your luck with a trusted and regulated bookie.

However, while the above sports betting wins are certainly mind-boggling, remember that any winnings you make should never be considered your principal source of income. Treat online gambling for what it is – a fun pastime rather than the principle source of your livelihood.

Always bet responsibly!

Further Reading

  1. Best India Horse Race Betting Sites (2022) In this guide, we take you through the top 10...
  2. Maximum Payouts for India’s Top Betting Sites (2022) Let’s face it – the goal of sports betting is...
  3. Your Guide to Cheltenham Betting Odds and Tips (2021) The Cheltenham Festival, rightly billed ‘The Greatest Show on Turf',...

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