The Craziest Bets in Sports History (That Won)

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Sports betting is quite a thrill, especially if you really like the team you’re betting on and are emotionally invested. It can pay out big time but you can also end up losing a lot of money. In the case the latter happens, things might not be looking as bright as before, that is why smart bets should be placed and not emotional ones, even though it means not betting on your team.

There are, however, the stories of winners of huge prizes who bet on the most unexpected teams or players. These stories are told and they spread with the wind. If you’re not as good to listening to the wind as others may be, here are some of those stories.

Billy Walters – Sports Betting Genius

Billy Walters was a professional poker player at one point. That requires a lot of skill and research and no small amount of control over your emotions. He also showed us that research does play a great role in sports betting.

The Indianapolis Colts were playing the New Orleans Saints in the Super Bowl finals in 2010. Billy used his four decades of betting and gambling experience to place a bet on the Saints, which were deemed as the less favorable ones to win. He did not bet 20 or 50 or even 500 dollars but 3.5 million dollars. The Saints won 31 to 17 and got their first Super Bowl trophy. While no one is sure how much money Billy won for that bet, everyone assumes it’s a lot, given the initial bet and the odds being against the Saints.

Research and experience can take you a long way.

Mick Gibbs – Winning a Bet for a New Roof

Mick Gibbs has a hobby and it’s betting. This punter is no stranger to winning money when the odds are really against him.

Back in 1999, he won 157,000 pounds when he predicted 9 football games’ outcomes. This bet was just a warm-up, however. In 2001, he placed only 30 pence and his betting slip had 15 games worth of odds. They were really against him, so much that it wasn’t really expected that he’d win anything.

It all changed when in the last game of his betting slip, Bayern Munich’s goalkeeper defended the last penalty shot and won Bayern the game. Valencia was sour on that day but Mick Gibbs was a very happy man with 500,000 pounds in his pocket.

He repairs roofs for a living, but with that kind of money, he can buy a roof that does not need repairing.

Darren Yates – The Faithful Punter

Darren Yates bet 67.58 pounds on his favorite jockey, Frankie Dettori. Dettori himself wasn’t really feeling that he might take any of the races, at most two, per his interview. However, on September 28th, 1996, he managed to win all seven races and make a lot of people happy, more specifically, his fans.

While there were unhappy bettors, Darren Yates, the one who bet the most, won the most, 550,823 pounds of faithful pounds.


These are some of the greatest sports bets that paid out in the end, showing that both meticulous research and experience, as well as having faith in your favorite can win you money. There are times when it doesn’t work out, however, but these were not those times.