Top 10: Biggest Sports Betting Wins In History (2022)

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!