5 Of The Craziest Sports Betting Payouts Of All Time

Sports betting, like any other form of gambling, gives bettors massive win potential. Like a slot jackpot or hitting a progressive side bet on a Las Vegas table game, sportsbooks can yield larger-than-life returns for certain lucky bettors. It may take a lot of guts to front a hefty wager, but when it pays off, the financial windfall can be life-changing. 

Sports betting’s long international history, plus the recent US adoption of sports wagering, has led to many impressive, sometimes downright crazy wins. Take a look at some of the biggest and wackiest sports betting wins of all time.

Family Is A Safe Bet

Pro golfer Rory McIlroy won the 2014 Open Championship in Merseyside, England, a first for one of the sport’s rising stars. 

Nobody predicted McIlroy’s rise through the ranks of the PGA Tour like his father, Gerry. Just about 10 years earlier, Gerry McIlroy and a few of his friend pooled their money and bet nearly $700 that Rory (who was 15 at the time) would win the Open within the next 10 years. The odds were 500-1

Right in the nick of time, Rory delivered. He won the Open in 2014, just one year before the 10-year window expired. His dad and his buddies? They earned $342,000. Cue a family-wide celebration. 

Football Parlay Payday

There are few things more satisfying in the world of sports betting than winning a parlay. Selecting even three or four outcomes correctly is cause for celebration (and a nice payout). Even a winning 7-pick parlay would be an accomplishment to be proud of. But how about 15 correct picks? In 2015, Tayla Polia managed it, earning a huge payout. 

Then 26-year-old Vegas-native Polia built a $5 parlay and selected the outcomes of 15 games. Some sources even report that this was her second-ever bet and she had no knowledge of point spreads at the time, making the wager even more impressive. 

The 2015 NFL season brought Polia a string of wins thanks to savvy (or lucky) picks. In one case, Polia thought she lost the bet when the Giants lost a game but managed to cover the spread. That added to her surprise when the bet paid out a whopping $105,000.

An $82K Odds Mistake

If you’ve played Monopoly, you know how amazing it feels when you draw the famous “Bank error in your favor–collect $200” Community Chest card. 

One FanDuel customer experienced that same feeling but with a much higher reward (and with real, non-monopoly money, no less!). Anthony Prince of Newark, New Jersey placed a $110 bet late in a Broncos-Raiders NFL matchup in 2018. FanDuel’s platform mistakenly offered 750-1 odds on the bet, which Prince won. 

Even though the odds were offered in error, FanDuel paid the full $82,000 to Prince. The company paid out similar wins for other bettors who took advantage of the long odds. 

Golden Goals For Gibbs

Mick Gibbs, an English roofer, makes this list for two crazy wins in the late 90s and early 2000s. 

In 1999, Gibbs wagered 2.5 British pounds (just over $3 USD) on a 9-leg European soccer accumulator (parlay). He selected every match outcome correctly, netting nearly $200,000. 

Two years later, Gibbs scored another big win, this time on a 15-stage parlay. He bet around $0.40 with odds of 1,666,666 to 1. The bet came down to the wire, with the final game on the ticket (Bayern Munich vs. Valencia) going to penalty kicks. Bayern Munich logged a game-winning save and netted Gibbs $633,000. 

Tiger’s Return Nets Bettor $1 million

11 years had passed since Tiger Woods had won a major championship. But that didn’t stop gambler James Adducci from betting on the star’s comeback. Adducci reportedly traveled to Vegas with $85,000 cash and bet on Tiger to win the 2019 Masters at 14 to 1 odds. 

Tiger went on to win the Green Jacket, and Adducci nabbed a cool $1.2 million. 

About the Author

Cole Rush

Cole Rush is a Chicago-based freelance writer in the gambling, media, and entertainment space. His work has been showcased in various gaming industry magazines and online columns. Prior to freelance writing, Cole spent seven years in communications at a gambling and lottery supplier. Cole writes for a number of online and print publications, including The Quill To Live, a book review site.