Sports Betting Wins: All-Time Biggest Payouts


The biggest sports betting wins of all time will blow your mind. 

While winning a few hundred dollars on the weekend will satisfy most people, a handful of lucky punters have become millionaires overnight thanks to sports betting. 

Did you know that one bettor landed a $3.5 million payout on the Super Bowl? How about the UK heating engineer who turned £2 into £1.5 million with the help of six horses? 

Without further ado, let’s check out some of the biggest sports betting wins in history. 

Billy Walters Bets $3.5 Million on Super Bowl XLIV 

When the New Orleans Saints and Indianapolis Colts were confirmed as the Super Bowl teams in 2010, there was a clear favorite. All the bookies expected Indianapolis to triumph, leaving New Orleans as the underdog. 

However, Billy Walters had other ideas. The well-known gambler placed an audacious $3.5 million bet on the Saints, risking a crazy amount of money. 

Thankfully for Walters, New Orleans upset the odds. The Saints shocked the Clots and took home the 31-17 victory, leading to one of the biggest sports betting wins of all time. 

Vegas Dave Pockets $2.5 Million Thanks to the Kansas City Royals 

If you already know a thing or two about sports handicapping, the chances are that you’re familiar with Dave Oancea. Better known as Vegas Dave, the elite gambler has claimed countless betting wins over the years. 

In 2015, the Kansas City Royals hadn’t won the World Series in three decades. Seeing value in Kansas City’s +3000 odds, Vegas Dave backed them to clinch the title. 

After spreading his $140,000 bet across 15 different casinos due to sportsbooks not wanting to take all his money, Vegas Dave’s hard work paid off. The Royals defeated the New York Mets to win the World Series, landing Vegas Dave a giant $2.5 million payout. 

UK Heating Engineer Secures One of the Biggest Betting Wins of All-Time 

While Billy Walters and Vegas Dave are well-known names in the sports betting industry, Steve Whiteley is not. That’s because Steve Whiteley was a 61-year-old heating engineer when he secured one of the biggest sports betting wins in history. 

In 2011, Whiteley made use of a free ticket to the horse races. To make things a little more interesting, he placed a £2 parlay containing six selections. 


  • Semi Colon (+200) 
  • Lundy Sky (+500) 
  • Black Phantom (+1200) 
  • Lupita (+1200) 
  • Ammunition (+1600) 
  • Mr Bennett (+1600) 

Remarkably, all six of Whiteley’s selections won, giving him a life-changing payout of £1.5 million. Whiteley even backed a horse that had lost in all of its 28 races in the past, making his bet even more extraordinary. 

Lucky Fertilizer Salesman Turns £0.50 Into £1 Million 

Steve Whiteley is not the only British man in his sixties to turn a measly sum of money into a fortune. Three years before Whiteley’s success, Fred Craggs enjoyed one of the biggest sports betting wins of all time. 

The fertilizer salesman from Yorkshire visited his local William Hill betting shop and placed a tiny £0.50 parlay on eight horses. Little did he know that this bet would change his life forever. 

Funnily enough, Craggs wasn’t even aware of his triumph until he returned to the bookie for another bet. The 60-year-old would have won £1.4 million if it weren’t for betting limits, but he still walked away with a cool £1 million. 

Gutsy Punter Lands Monster £1 Million Parlay 

Due to the vast range of factors that influence each hole, golf is known as one of the most difficult sports to bet on. Still, that didn’t stop one lucky gambler from selecting the outright winner of four golf championships in 2021. 

Not only did the punter predict the winners of four golf championships, but they also predicted the results of two Euro 2020 soccer games. Five of the parlay’s six legs came to fruition, leaving one agonizing leg. 

Priced at +3500, Harris English needed to win the Travelers Championship for the bet to land. After making a dramatic 28-foot putt on the final hole to send the championship to a sudden death, English finally secured his victory with a birdie. 

As a result, the lucky bettor turned £13 into £1,039,554, registering one of the biggest-ever sports betting wins. 

Charles Barkley Lands One of the Biggest-Ever Sports Betting Wins 

Charles Barkley is best known for his exploits in the NBA. The ex-forward picked up countless accolades during an illustrious 16-year career, representing the Philadelphia 76ers, Phoenix Suns and Houston Rockets. 

But did you know that Barkley is also known for collecting one of the biggest sports betting wins of all time? 

Ahead of the Super Bowl in 2002, the New England Patriots were 14-point underdogs against the Los Angeles Rams. Nevertheless, that didn’t deter Barkley, who placed $500,000 on the Pats to defeat the Rams. 

Barkley cashed out a walked away with $800,000. Further down the line, however, Barkley placed a $100,000 on the Atlanta Falcons to beat the Pats in Super Bowl LI, watching them throw away a 28-3 lead. You can’t win ‘em all, Charles! 

Are You Inspired By the Biggest Betting Wins in History? 

Every gambler dreams of winning millions, but only a select few turn their fantasy into reality. Of course, you need to be a smart gambler if you want to make a fortune, but you also need a ton of luck on your side. 

The biggest sports betting wins of all time are rarely emulated, but that shouldn’t deter you from giving it a go. If you’ve got a good feeling about an underdog or a big parlay, why not lay down a couple of dollars and see what happens? 

That said, we also recommend placing smart bets and building your bankroll over time. Lucky for you, Sports Hub is home to dozens of top handicappers who offer expert picks and predictions all year round!