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Home » Blog » biggest sportsbook wins of all time

The Ten Biggest Sportsbook Wins Of All Time Including Billy Walters And Charles Barkley

James Chittick
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We’ve counted down the top ten biggest sportsbook wins of all time, featuring NBA stars, professional gamblers and a few very lucky regular punters.

Any gambler dreams of winning big. The allure of hitting the jackpot is why we all like a flutter. But for the people on this list, their sporting picks came in bigger than anyone could imagine.

Sports betting is a unique market, with many believing they have worked out how to game the system, analyse data or use insider knowledge to win.

Some make a living from it, but others just got very, very lucky.

Either way, we’ve taken a look at some of the biggest sportsbook wins of all time.

Top Ten Biggest Sportsbook Wins Of All Time

10. Mick Gibbs – £500,000 from a £0.30 bet

A roofer by trade Mick Gibbs is tenth on our list of the biggest sportsbook wins ever. Just two years after another huge win, Gibbs put 30p on a 15-fold accumulator with incredible, 1,666,666/1 odds.

Gibbs’ first 14 picks all came in, leaving the UEFA Champions League final as his last game. The match between Bayern Munich and Valencia went all the way to penalties, which was no doubt agony for the roofer.

But Bayern held their nerve, and Gibbs pocketed a half million pounds, having bet no more than the price of a Cadbury’s Freddo.

9. Darren Yates’ Magnificent Seven – £550,000 from a £62 bet

Next is Darren Yates, whose 1996 win would see him become a majro name in horse racing. Known as the ‘magnificent seven’, Yates successfully wagered £62 on jockey Frankie Dettorri winning each of his seven rides at Ascot that day.

8. Anonymous punter – £585,000 from an £0.80 bet

Eighth place goes to an anonymous entry. In November 2011, an unknown punter in Malta placed 80p on a 19-fold accumulator with William Hill.

At odds of 683.738/1, all 19 predictions were correct, finishing with Liverpool’s last-gasp winner against Chelsea to net out mystery Maltese $585,000.

7. Charles Barkley – $800,000 from a $500,000 bet

A well-known betting lover, former NBA Champions Charles Barkley is a big name in sports betting. A regular to big wins, his greatest ever came when he backed the New England Patriots to win the Super Bowl.

Although the Tom Brady era makes this sound an obvious choice, they were unfavoured at the time, and in 2002 were 14-point underdogs to the then St. Louis Rams (now Los Angeles).

With Brady earning his first Super Bowl ring, he also earned Barkley $800,000 (around £608,000)

6. James Adducci – $1.2 million from an $85,000 bet

A famous bet, James Adducci bet on Tiger Woods’ 2019 Masters victory, his first major championship win for 11 years.

Putting $85,000 on a man who’d won nothing in a decade and been through numerous scandal’s may seem crazy to most, but that’s why Adducci is on this list and the rest of us aren’t.

Wether brave or foolish, his bet paid off, earning him $1.2m (around £760,000) and setting a new record with William Hill for an individual payout.

5. Mike Futter – £800,000 Betting On His Own Horse

It’s a name known by many in the betting world. Just the letter ‘L’ away from one of the best names in gambling history, Futter managed to win big by betting on his own horse.

In 2003, he backed Monty’s Pass, who earning him a huge payday. Futter took home £348,000 as the horses owner, as well as an additional £400,000 for betting on the horse at odds of 40/1 down to 16/1.

“I’ve had some fantastic bets and fantastic days but this is one I will never forget,” said Futter after his monumental day.

4. Fred Craggs – £1 million from a £0.50 bet

Yorkshire fertiliser salesman Fred Craggs made on of the biggest sportsbook wins of all time when he placed just 50p on an eight-fold accumulator.

Picking horses from races around the world, Craggs won a cool £1m. Amusingly, Craggs didn’t even realise he had won at first, only noticing when he next visited the bookies for another bet.

What’s more, he would have won £1.4m if he’d chosen a no-limit bet. Still ,we doubt he was too upset after picking up his seven-figure sum.

3. Steve Whiteley – £1.5 million from a £2 bet

Now we’re on to the podium places. In third spot is 61-year-old heating engineer, Steve Whiteley. In 2011, he took a free ticket to the horse racing and lumped £2 on a 6-fold acca.

Incredibly, all six came in on the day, including one horse which had lost all of its 28 previous races. Whiteley went home with £1.5m and the story of a lifetime.

2. Vegas Dave – $2.5 million from a $140,000 bet

“Vegas” Dave Oancea broke records with a massive 2015. His second successful bet came a week into the 2015 MLB season. Oancea picked the Kansas City Royals to win the World Series, at odds of 30/1.

His bet of $140,000 took some doing, having to be split across 15 different casinos as none would take it in one sum.

Many called him crazy for lumping on such a huge sum, but he had the last laugh for sure. The Royals defeated the New York Mets to win the World Series and earn Vegas Dave $2.5m (around £1.9m)

1. Billy Walters – a successful $3.5 million bet

And last but not least, Billy Walters tops out list of the biggest sportsbook wins in history. A household name to followers of the sports betting industry, Walters won his biggest bet of all in 2010.

The New Orleans Saints faced off with the Indianapolis Colts at Super Bowl XLIV, with Walters backing the underdog Saints who went on to win 31-17 and secure their first Super Bowl title.

Walters started his gambling journey on the poker scene, before earning fame for his record-breaking winning streak in sports betting.

Proof beyond doubt that there’s skill to sports picks, Walters has made a fortune for himself over the years. But when he placed $3.5m (around £2.7m) on New Orleans, he made not only the biggest sportbook win ever, but one of the biggest betting wins of any kind in history.

James Chittick
James Chittick

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