The Biggest Sports Betting Wins of All Time

biggest sports betting wins ever

While most of us can only dream of hitting a 20-leg parlay and launching ourselves into early retirement with a multi-million dollar payout, there are a few lucky punters out there who have done just that.

Biggest Sports Betting Wins

Let’s take a look at some of the biggest sports betting wins of all-time.

1. Billy Walters’ Legendary NFL Bet

Billy Walters’ Legendary NFL Bet

Billy Walters, often referred to as one of the most successful sports bettors in history, secured a legendary win in 2010. Walters is known for his strategic and calculated bets, often involving sophisticated computer analysis.

His most famous victory came when he placed an $8 million bet on the New Orleans Saints to win the Super Bowl XLIV. The Saints triumphed over the Indianapolis Colts, earning Walters a multimillion-dollar payday.

Walters’ incredible win underscored his reputation as a betting savant and cemented his legacy in the sports betting world.


2. The “Vegas Dave” UFC Bet

Dave Oancea vegas dave

Dave Oancea, better known as “Vegas Dave,” made headlines in 2015 with his extraordinary UFC bet. Oancea wagered $1 million on Holly Holm to defeat the undefeated Ronda Rousey at UFC 193.

Holm, a massive underdog, pulled off one of the biggest upsets in UFC history by knocking out Rousey in the second round.

This victory netted Oancea a staggering $2.5 million.


3. Leicester City’s Premier League Miracle

Leicester City’s Premier League Miracle

One of the most astonishing sports betting stories involves Leicester City’s 2015-2016 Premier League title win. At the beginning of the season, bookmakers gave Leicester City 5000-to-1 odds to win the Premier League.

Despite the astronomical odds, a few optimistic fans placed bets on their beloved team. One such bettor, who wagered £20 ($26), walked away with £100,000 ($130,000) when Leicester defied all expectations and clinched the title.


4. Phil Mickelson’s Baltimore Ravens Bet

Phil Mickelson’s Baltimore Ravens Bet

Professional golfer Phil Mickelson is known for his prowess on the golf course, but he also made a significant mark in the sports betting world. In 2001, Mickelson placed a $20,000 bet on the Baltimore Ravens to win the Super Bowl at 28-to-1 odds.

The Ravens went on to dominate the New York Giants in Super Bowl XXXV, resulting in a $560,000 payout for Mickelson.


5. Anonymous Bettor’s World Cup Windfall

In 2010, an anonymous bettor placed a £500 ($650) wager on a series of World Cup matches, predicting the correct scores for eight games. The odds of winning were calculated at an astonishing 683,738-to-1.

When all the predictions came true, the bettor walked away with a jaw-dropping £350,000 ($450,000).


6. Charles Barkley’s Super Bowl Bet

Charles Barkley’s Super Bowl Bet

NBA legend Charles Barkley is no stranger to sports betting, but his most famous win came from an NFL bet. In 2002, Barkley placed a $500,000 bet on the New England Patriots to win Super Bowl XXXVI against the St. Louis Rams.

The Patriots, considered underdogs, won the game 20-17, earning Barkley $800,000.


7. Steve Whiteley’s Horse Racing Triumph

Steve Whiteley betting win

In 2011, Steve Whiteley, a heating engineer from Devon, England, turned a modest horse racing bet into a life-changing sum.

Whiteley placed a £2 ($2.60) bet on a series of six races at Exeter Racecourse. Remarkably, he correctly predicted all six winners, one of which had odds of 12-to-1. Whiteley’s bet, known as a “Scoop6,” earned him a staggering £1.45 million ($2 million).


8. Fred Craggs’ 60th Birthday Surprise

fred craggs betting win

Fred Craggs, a fertilizer salesman from Yorkshire, England, received an unexpected birthday gift in 2008. Craggs placed a 50p ($0.65) accumulator bet on eight horse races.

To his amazement, all his picks won, and his bet, placed at odds of 2,000,000-to-1, turned into a £1 million ($1.3 million) windfall.

Want to get more specific? Check out some of largest wins betting on NHL, the biggest betting wins on NFL and the largest amounts won betting on MLB.