Crazy Sports Bets That Won Major Money Prizes

There are many unbelievable stories of people winning life-changing money through sports betting. Some have won by correctly picking the winner of a big game, while others have made more outrageous bets that have somehow paid off. CNN reported on some of the craziest sports bets that have won major money prizes.

Sports betting is a pastime enjoyed by many, whether it’s putting a few bucks on the big game or betting with Sbobet on your favorite team to win the championship. Crazy sports bets seem to be all the rage these days. From betting on which team will win the Super Bowl to which player will score the most touchdowns, there is no shortage of ways to place a crazy sports bet. While most of these bets will never pay off, there are a few that have actually won major money prizes. Here is a list of some of the craziest sports bets that have paid off:

Yorkshire Man Beats

You might not think a fertilizer salesman could be a high roller, but Fred Craggs proved us all wrong. In 2008, he celebrated his 60th birthday by making an eight-horse parlay bet. Amazingly, he won the bet, beating the 2,000,000-to-1 odds and taking home a £1 million prize.

Since then, Fred has become something of a legend in the world of sports betting. He’s not the only one to have made a crazy bet and won big, though. There have been plenty of other instances where people have beaten long odds to win huge sums of money.


Roofer Beats

Mick Gibbs, a roofer from Australia, placed a 15-team parlay bet in 2001 that seemed impossible to win. Gibbs wagered on a number of sporting events, including Australian Rules Football, rugby union, and cricket. Incredibly, all 15 of Gibbs’ selections won, and he beat the 1,666,666-to-1 odds to win a major money prize. Gibbs’ story is just one of many incredible tales of sports bettors beating the odds and winning big.

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Gerry McIlroy Bets

Rory McIlroy is one of the most successful golfers in the world, with four Major titles and 14 total PGA tournament wins. He’s also the son of Gerry McIlroy, who made a pretty incredible bet on his son’s future success.

Gerry McIlroy bet that Rory would win the British Open within 10 years, and he ended up being right! Rory won the British Open in 2014, just four years after his father made a bet.

While it’s certainly an impressive feat, it’s not the only time someone has won big money by betting on a crazy sports outcome.


$14 Million Winnings from the “Sir Ride a Lot” Rides World Series

When it comes to sports betting, there are always going to be those who take things to the extreme. In 2017, a man from Eastern European toured Las Vegas and bet on World Series games between the L.A. Dodgers and Houston Astros. The man, who went by the nickname “Sir Ride a Lot,” ended up winning a whopping $14 million.

While it’s certainly impressive that he was able to walk away with such a large sum of money, it’s also important to remember that this is an extreme example. For the majority of people who choose to bet on sports, the goal is simply to have a little bit of fun and maybe make a few extra dollars. However, there are always going to be those who take things to the next level.

Woman Wins £574,278 on a £1 Parlay

A housewife from Kent, England, won over half a million pounds from a soccer accumulator bet in the early 2010s. This bet is similar to an American parlay bet, where multiple bets are placed on different games, and the winnings from each bet are used to finance the next bet. If anyone bet loses, the entire bet is lost. The housewife’s husband had been making these types of bets for years, and she decided to try it herself. She ended up winning £574,278 from a £1 bet. This is just one of many stories of people winning big money from sports bets.


Billy Walters Wins $3.5 Million

Billy Walters, a professional gambler, won a $3.5 million prize in 2012 after placing a bet on the New York Giants to win the Super Bowl. The winnings resulted from a series of earlier bets that Walters had placed on the Giants.

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Walters is not the only one to have won big by betting on sports. A number of people have made large sums of money by placing bets on sporting events.

Some of these bets have been on individual games, while others have been on the outcomes of entire seasons. In either case, the people who have won these bets have walked away with some serious money.

Combined $1.5 Million Winnings from 50 Cent Wins Two Giants Bets

In recent years, we’ve seen a number of celebrities get involved in some pretty crazy sports bets. But none may be crazier than 50 Cent’s recent wager on the New York Giants.

The rapper, whose real name is Curtis Jackson, is a long-time Giants fan. And he put his money where his mouth is, betting a combined $1.5 million on the team to win their two most recent games.

Incredibly, he won both bets, netting himself a cool $1.5 million in the process. So, what’s next for the New York-born rapper and self-proclaimed “biggest Giants fan in the world?”

Only time will tell. But one thing’s for sure: 50 Cent is now a very rich man thanks to his risky (but ultimately successful) bet on his beloved Giants.


Man, Bets on Jockey Winning Seven Races in One Day

When it comes to horse racing, few jockeys are as revered as Franki Dettori. The Italian-born jockey has had an illustrious career, winning some of the most prestigious races in the world.

In 1996, Dettori pulled off one of the most amazing feats in horse racing history, winning all seven races at Ascot in a single day. Amazingly, Dettori was a long shot at winning all seven races that day.

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That’s not the only time Dettori has pulled off a big win. He’s also won major money prizes for other crazy sports bets.