5 Biggest Sports Betting Wins of All Time

There are few thrills in life that are quite as exciting as winning a big sports bet that not many other people saw coming. No matter the sport, it’s always fun to win, but especially when you win big. In a handful of cases, some bets that have been as low as $50 have turned into seven figures and cracking the code of the sports betting world. Here are five of those times when bettors defied the odds and won more than anyone else.

Anonymous ($1.13 Million)

Parlays can be a cheap way to have a lot of fun, and those of us who live in places where sports betting is legal to have often thrown a couple of dollars at one. Have you ever felt like you could turn $50 into more than $1.1 million, though?

That’s what one bettor did in November 2021 through the BetMGM app, and it wasn’t just a two or three-game parlay, either. He placed his $50 on a 15-game parlay across several different sports. The parlay got off to a good start when the Vegas Golden Knights of the NHL won, and the 15th game had the Baltimore Ravens winning straight-up. They did just that, earning the anonymous bettor over $1.1 million.

James Adducci ($1.2 Million)

Imagine winning over $1.2 million on your very first sports bet. That’s what happened to Wisconsin native Jim Adducci during the 2019 Masters when he placed an $85,000 bet on Tiger Woods to win his first major in several years.

Woods, who was actually a massive longshot at the time due to injury and near-retirement, ended up shocking the world by winning the green jacket. He also made Adducci a wealthy man, which was good because he had to sell his Amazon stock to get out of debt and make the wager.

Dave Oancea ($2.5 Million)

Saline, Michigan is a long, long way from Las Vegas, but Dave Oancea has become so ingrained with Sin City that he’s now known as Vegas Dave. Oancea has made a career off of betting on sporting events in Las Vegas, and in 2015, he became a household name across the nation thanks to the World Series run of the Kansas City Royals.

The Royals came into the season as a pretty big longshot to win it all at 30-to-1. The man who grew up rooting for the Chicago Cubs quickly changed his allegiance for just one year, as he placed over $83,000 on the Royals to win it all. When they got to the World Series, Vegas Dave started showing up to games with a Royals jersey on, and the team didn’t disappoint as they earned him $2.5 million in the largest futures win in American history.

Billy Walters ($3.5 Million)

In the world of gambling, there are few names that are quite as well-known as Billy Walters. Walters was born and raised in Kentucky but has spent much of his adult life making bets in Las Vegas. Because of his success, it’s estimated that Walters has accumulated a net worth of over $100 million, with almost all of it coming from betting.

There have been a handful of instances in which Walters has won seven figures from a singular sports bet, including more than $2 million for a 2007 football game between USC and Michigan. However, his biggest win came during Super Bowl XLIV when he put all of his confidence in the New Orleans Saints to win their first championship. The bet paid off as the Saints defeated the Colts, earning Walters a cool $3.5 million.

Mattress Mack ($75 Million)

In the Houston, Texas area, everyone knows the name Jim McIngvale, though they simply refer to him as Mattress Mack. McIngvale owns the Gallery Furniture chain of stores in the metro area, and has become a local legend over the years. Not only is he known for his stores, but he’s also known for putting huge money on sports betting to hedge his funds from the massive sales that he does every year.

In 2022, Mattress Mack put up the largest bet ever on a mobile phone, placing $4.5 million on the Cincinnati Bengals to win Super Bowl LVI. The team would end up losing, but McIngvale has had a much, much bigger win. In the same year, McIngvale placed a large wager prior to the 2022 MLB season for the local Houston Astros to win the World Series. The team ran through the playoffs rather easily, and Mattress Mack took home an ultimate payout of $75 million, the highest payout in sports betting history.