Biggest Sports Betting Wins

If you think you know what it means to be a high roller, just wait until you see what we have in store for you in this article. This is a chronicle of some of the most insane gambles people have made in the past which paid off and made them rich.

Read about the unbelievable amounts that were put on the line for sports gambling, the individuals behind the bets and how much they realized from it.

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Kansas City Royals Future – $2.5 Million

Vegas Dave is one punter who is not shy to talk about his successes in the online gambling industry. While some people doubt the truthfulness of his claims, the fact remains that he has been able to land some massive wins via online betting.

His most significant bet, which was on the Kansas City Royals to win the World Series at 30/1, is the most daring so far and boy did it yield profit! The bet was too risky that even bookies refused to accept his bet money.

However, Vegas Dave wouldn’t take no for an answer. His next move was to divide the bulk money he wanted to bet into 15 places and distribute them to 15 casinos. As history would have it, the Royals won the World Series and Vegas Dave became $2.5 million richer.

Tiger Woods Masters Bet – $1.2 Million

Tiger Woods is one of the living legends in the world of sports. It is no secret that he is extremely well accomplished. He was the number one golfer for almost 12 years, which is a remarkable feat. However, sometime in 2010, the golf star started to lose form. A number of factors contributed to this, including his infamous infidelity which led to his divorce.

The quality of his performance decreased over the years, it made no sense why anyone would bet on him to win any competition, let alone put as much as $85,000 on the line. But that’s exactly what James Adducci did. Adducci somehow convinced his wife to support an $85,000 wager on Tiger Woods to win the 2019 Masters. This bet, which was placed at the William Hill sportsbook with 14-1 odds, was a huge success and Adducci netted $1.2 million.

This win became a record-breaker at the William Hill sportsbook and is regarded as the biggest paid-out future bet. For yet another shocker, you wouldn’t believe that this was Adducci’s first-ever sports bet? That’s mind-blowing!

New England Patriots Super Bowl Bet – $800,000

It’s not every day that one comes across a sports star who is also a gambler. That’s the deal with American former professional basketball player, Charles Barkley, who isn’t just a celebrated sportsman, but also a serious gambler. His story is fascinating.

Barkley has never been shy about his gambling habit and always open about his wins and losses in gambling. That’s how we got to know about his $500,000 win from betting on the New England Patriots to win the Super Bowl in 2002.

Being 14 point underdogs, the chances of the New England Patriots clinching a win were very unlikely. However, Barkley stuck to his guns and remained unshaken in his decision. Well, in the end, it all paid off when the Patriots emerged as the winners and Barkley took home $800,000.

Baltimore Ravens Super Bowl Future – $560,000

Even the top athletes of this world need a way to blow off steam once in a while, and for the seasoned golfer, Phil Mickelson, it is gambling. For those who don’t know him, Mickelson, also known as Lefty, is a highly ranked golf player with six major championships under his belt and many other outstanding performances.

He threw his weight behind the Baltimore Ravens to win the Super Bowl for the 2000/2001 NFL season. And to put his money where his mouth is, Mickelson coughed out a whopping $20,000 to bet on them.

As if he saw into the future, his prediction turned out to be accurate with the defeat suffered by the New York Giants at the hands of the Ravens, which earned Mickelson a whopping $560,000.

Leicester City Premier League Future – £200,000

No one could see far enough to predict the outcome of the 2015 premier league season, except for a man named Leigh Herbert.

While eyes were on the usual suspects, Manchester United, Tottenham, Arsenal, Manchester City and other big teams to win the title, Leicester City took everyone by surprise by claiming the top spot on the league table.

Herbert placed a £100 bet on an outcome that would become one the biggest upset wins in sports history. Despite having a preseason odds of 5,000/1, Leicester City went ahead to dominate some of England’s biggest teams and in the end, their victory led to a £200,000 payout for Leigh Herbert. What an unbelievable win!


The odds of becoming a millionaire betting on sports are real, but you must consider many factors and have a lot of statistical information to be able to achieve a result of this magnitude, because the world of sports is uncertain. In addition you should always consider betting only the money you are willing to risk, so you do not fall into debt or problems derived from the misuse of gambling.

No, our recommendation is always to bet at licensed bookmakers, as they comply with the necessary laws, which allows users to have a higher security for their personal and banking data.

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