5 Of The Biggest Sports Betting Wins Of All Time

It seems as though as long as there's been sports, there have been people wanting to place bets on their outcomes. According to the book "The Business of Sports Betting," sports betting dates back as far as 3000 to 4000 B.C. and the ancient Egyptians, while the people of ancient Greece some two millennia later likely bet on the first Olympic Games (the first was held in 776 B.C.). This said, if you want to talk about the biggest sports betting wins of all time, you'll have to fast forward some ~2,800 more years, as they're all from the 2000s.

In our list, three hail from the United States, where sports betting only became legal in 2018 when the Supreme Court overturned the Professional and Amateur Sports Protection Act of 1992. (Here are the states that allow sports betting today.) The other two big wins are British bets, and both of them are on horse races.

Irish businessman Mike Futter employed games of chance in both his business model (he owned a half-dozen bingo halls) and lifestyle (he was an avid gambler). That really paid off for him when he and four associates invested in a racehorse named Monty's Pass, which went on to win the Aintree Grand National in 2003.

Futter made bets with about eight bookies. His strategy involved three hours of studying the lineup for the first race and looking for any slight edge — in the case of the Grand National, Monty's Pass ran slightly faster on the left side of the track than the right. While not the favored horse to win, with odds of 40 to 1, 50 to 1, and 66 to 1, that fact only served to make Futters' stake on the horse that much more lucrative when Monty's Pass finished the race in first place.

Mike Futter walked away £800,000 (or $1.1 million at the time) richer. While winning that kind of coin on a sports bet is akin to winning the lottery, it doesn't sound like Futter became a lottery winner who ends up broke since he had a plan for his winnings: investing in property in Donaghadee, a small town in Northern Ireland.

In 2019, the golf legend that is Tiger Woods was no longer the favorite to win the Masters that year (it had been 14 years since his last green jacket in 2005). Plagued with over a decade of losses on the green, chronic injuries, and the personally as well as financially painful dissolution of a marriage that still counts as one of the most expensive divorces in sports history, it was no longer a given that the athlete could perform (and win). That makes James Adducci's 2019 bet that much more impressive, as he didn't have a lot of experience with sports betting at all prior to his Woods bet.

Money Digest notes that investing is one of the easiest ways to become a millionaire, yet, just as important as having the discipline and know-how to invest is knowing when it's time to sell a stock. Thanks to a wise investment in Amazon, Adducci was able to sell over $55,000 worth of stock to help finance his $85,000 bet on Tiger Woods' win at the 2019 Masters. He was $25,000 in debt a week before the tournament, according to Golf Digest.

Most people would have paid off their debt first. Instead, Adducci took a 14-to-1 bet on Woods that helped him win $1.2 million. With his bet, he also beat records at the time for the largest payout for a future sports event.

The horse track has given more than one bettor a huge win, and in the case of Steve Whiteley, it was one of the biggest sports betting wins of all time. Back in 2011, Whiteley was a 61-year-old, working-class heating engineer from North Tawton in Devon, England. While claiming to visit the racetrack a maximum of two times a year, Whiteley tried his luck on a £2 bet at Exeter Racecourse in 2011: a £2 bet on six races run by horses he chose randomly. No complicated stats were studied nor algorithms considered, and at least one of the selected horses had odds of 12-to-1 against it to win.

Whiteley even balked at the idea of paying the equivalent of just over $40 for a ticket that would allow him entry to the track and two selections in each race, instead opting for the one horse in each race. Utilizing a promotion that gave free tickets to him and six friends, Whiteley had very little to lose and everything to gain after stepping off of the bus that he arrived at the races on. When all six horses he chose won all six of their races, Whiteley hit the biggest Tote Jackpot at the time and he left the track with the equivalent of $1.9 million.

With a nickname like "Vegas Dave," it would be fair to assume that this is someone with a serious history of gambling. In Dave Oancea's case, you'd be right on the money, so to speak. A future sports better extraordinaire, Oancea has big wins and losses to his credit. Along the way, Oancea picked up a gambling addiction that ended in a two-month round of Gambler's Anonymous meetings. Not only did Oancea bet away his personal savings, but also his parents' — demonstrating the importance of knowing what to do if a loved one has a gambling problem. After getting help and picking himself back up, Oancea went back into sports betting with a renewed sense of discipline.

Basing his bet on the Kansas City Royals on their performance the previous year, Oancea went against the bookies and took 30-to-1 odds with $100,000 in favor of the Royals winning the 2015 World Series. In total, he placed 26 bets, as reported by The Kansas City Star at the time. And he had to split his bets across multiple casinos due to the risk of coverage for a single casino, even though the odds were heavily not in Oancea's favor.

While there were several opportunities for Oancea to cash out and run — at one point he could've walked away with $750,000 — he stayed the course. A total of $2.5 million was the payoff, a sports betting win so large at least one casino, the Westgate Casino, changed its sports-betting policy.

Last but far from least, we have Billy Walters, whose sports betting win may explain how much people bet on the Super Bowl these days. Starting out playing his hand as a poker player, Walters pivoted to sports betting in 2010. His storied career as a gambler in Vegas had him crossing paths with actual mobsters, robbed at gunpoint and forced into the trunk of his car, as well as receiving unfriendly visits from bookies he owed thousands of dollars to, which he somehow managed to survive through.

Whether dumb luck or skill, Walters had already amassed a small fortune by the time he made his Super Bowl XLIV bet. As a result, he could afford to wager $4.5 million on the New Orleans Saints, the team least expected to win. It was the largest bet Walters ever placed, as he told Joe Rogan in February 2024.

While Walters has remained tight-lipped about his winnings, sources have speculated his net worth to be at least $200 million. Since winning that bet, Walters has done time in prison in one of the most scandalous insider-trading busts we've ever heard of, serving four out of five years of his term before being pardoned by former President Donald Trump. With a 57% win rate (breaking even is 52.4%, by the way), it's a safe bet this is probably one guy who knows how to deduct gambling losses from his taxes.