Famous Sports Betting Wins and the Stories Behind Them

sports betting

Sports betting is so wildly popular for a few reasons. The first one is easy—people love to watch sports (sorry for stating the obvious). The second reason is also a no-brainer: people love to win money. And last but not least, when you lay a bet on your favorite team and bring home the big bucks? That feeling is priceless. Any way you slice it, wagering on sports is a fun, albeit stressful, way to spend your time and your disposable income.

Since it’s such a beloved pastime, we thought it would be fun to replay some famous sports betting wins and the stories behind them. Some of them are actually famous people, and some are just ordinary Joes!

From long shots to upsets, these tales are not just about winning big money—they’re about the people behind the bets, their strategies, and sometimes, their unbelievable luck!

Charles Barkley

Charles Barkley’s NFL Bet

Basketball legend Charles Barkley is as well-known for his betting as he is for his prowess on the court. One of his biggest wins came from a $500,000 bet on the New England Patriots to win the 2002 Super Bowl. Despite being 14-point underdogs, the Patriots triumphed, earning Barkley $800,000. However, Barkley also experienced significant losses, like when he wagered $100,000 on the Falcons in a Super Bowl and watched them lose a 28-3 lead.


Parlay Payout

The world of football betting has seen its fair share of extraordinary wins. In 2017, an MGM bettor in Las Vegas put $8,500 on a 5-leg NFL parlay, including the Ravens, Patriots, Chiefs, Raiders, and Detroit Lions. The Lions’ 24-10 victory over the Giants clinched the parlay, resulting in a $250,000 payout, marking one of the largest parlay wins in sports betting history.

Vegas Dave

The Infamous ‘Vegas Dave’

“Vegas Dave” is a controversial figure in the betting world, known for both his brash claims and significant wins. His bet on the Kansas City Royals to win the World Series at 30/1 odds is particularly noteworthy. Dave spread his bets across 15 casinos, and when the Royals won, he took home $2.5 million. Another major win for Vegas Dave was his $20,000 bet on Holly Holm defeating Ronda Rousey in UFC 193. Holm, an 11/1 underdog, won, netting Dave $200,000.

leicester city

Leicester City Football (Soccer for the U.S. Readers)

This was one of the most surprising upsets in sports history. When Leicester City was poised to start their 2015 Premier League campaign, they were massive 5000/1 underdogs. However, one daring punter saw an opportunity, placing $131 on Leicester City to win it all. Astonishingly, Leicester City defied the odds, securing a victory and earning the bettor $262,000. This win wasn’t just about the money; it was a testament to Leicester City’s remarkable triumph over England’s football giants.

Phil Mickelson

The Duffer

In the realm of golf, Phil Mickelson’s reputation extends beyond the greens to the betting tables. Before the 2000/2001 NFL season, Mickelson, known for his gambling enthusiasm, wagered $20,000 on the Baltimore Ravens to clinch the Super Bowl at 22/1 odds. His prediction was spot on, as the Ravens emerged victorious over the New York Giants, netting Mickelson a cool $560,000.

Tiger Woods

Tiger Woods for the Win

Another golf legend, Tiger Woods, was at the center of a major betting win, not as a bettor but as the subject of the wager. Despite his legendary status, Woods was not considered a safe bet in recent years. However, James Adducci disagreed and convinced his wife to let him bet $85,000 on Woods to win the 2019 Masters at 14/1 odds. The gamble paid off handsomely, earning Adducci around $1.2 million, setting a record at William Hill for the largest payout on a futures bet. Remarkably, this was Adducci’s first-ever sports bet.

Tayla Polia

15-Leg Parlay Payoff

In yet another NFL betting story, Tayla Polia took a chance on a 15-leg NFL parlay, which included 9 favorites, 5 underdogs, and 1 over/under, with odds of 20,000/1. This was only her second-ever bet, and with just $5 on the line, she won $105,000. The rarity of hitting a 15-leg parlay is staggering, likely countable on one hand.

Richard Hopkins

Vroom Vroom

Moving over to the world of Formula 1, Richard Hopkins made a prescient bet in 1998 after witnessing a young Lewis Hamilton at a go-kart track. Hopkins wagered $262 that Hamilton would win a Grand Prix before turning 23 at 300/1 odds and becoming a world champion at 500/1. Hamilton’s ascent to becoming one of the greatest Formula 1 drivers fulfilled both bets, netting Hopkins $216,150.

billy walters

Underdogs Deliver

Billy Walters, a renowned sports bettor before his legal troubles, made a splash in 2010 by betting $3.5 million on the underdog New Orleans Saints in Super Bowl XLIV against the Indianapolis Colts. The Saints’ victory not only brought Walters a substantial win but also highlighted his sports betting acumen, reportedly earning $50-$60 million in a “good year.” Walters’ betting career, however, was overshadowed by his 2017 prison sentence for insider trading, although he was later confined to home due to the COVID-19 pandemic.


These famous betting stories are not just about winning some money, although that’s a nice bonus. They show us how exciting and unpredictable playing the odds can be and about the people who took big risks that paid off in a big way.

Some were wagering newbies and got super lucky, while others were more experienced and knew exactly what they were doing.

But what do they teach us most of all? That taking a risk every now and then might just change your life.

Matthew Buchanan
Matthew Buchanan

Matthew specializes in writing our gambling app review content, spending days testing out sportsbooks and online casinos to get intimate with these platforms and what they offer. He’s also a blog contributor, creating guides on increasing your odds of winning against the house by playing table games, managing your bankroll responsibly, and choosing the slot machines with the best return-to-player rates.