Sports betting has its highs and lows. There’s the thrill and intoxicating adrenaline rush that comes with every win but then there’s also that “heart-sinking” feeling that occurs when the odds aren’t in your favour. Try and follow this surreal guide to take you through the biggest losses in history and what to stay away from.

In this article, we’ll look at some of these gut-wrenching moments in history where punters not only lost a couple of dollars but shocking amounts of money.

  1. Vegas Dave’s ‘Cupcake’ Loss

David Oancea is a prominent sports bettor who has mostly had luck on his side. He is popular on social media and has always boasted about his winning streaks. In 2016, however, Oancea had to taste humble pie when he placed a $1 million wager.

The bet was placed on Miesha ‘Cupcake’ Tate at the UFC 200 (MMA champion). Things turned instantly sour when, within the first 16 seconds of the game, Tate’s opponent overpowered her and she walked away with a broken nose.

Oancea seemed to take the loss in his stride though and his social media posts to follow all showed concern for Tate and her injuries.

  1. Michael Jordan Plays an Expensive Hole

This NBA legend has always been an avid gambler. Jordan’s hobby soon became an addiction and this realisation hit home when he lost $1.2 million to a businessman after a 10-day golf and betting binge.

  1. Steven Richard’s Whopping Loss

Steven Richard’s is just your average British blue-collar worker. His name made the headlines, however, when what started as a lucky streak, quickly turned south.

Richards successfully predicted the winners of 12 rugby matches and raked in £38,970 with just a £10 bet. A week later, he decided to bet on one more rugby match, this time with a whopping $30,000 wager on Wales to beat Australia. But alas, Australia took the reigns and the punter’s winning streak was over.

  1. Birdman’s Double Whammy

Birdman takes his betting seriously but he never seems to take his losses as a warning. His wagers are always daring and have created quite the dent in his pocket. Luckily the hip-hop star has more than enough money to go around.

Looking at his major losses, Birdman first lost $1 million by placing his bet on the Pats during the Super Bowl XLV – they lost against the New York Giants.

Next, when Super Bowl LII came around, he made another huge loss by wagering $100,000 along with Philly rapper AR-Ab.

  1. Daredevil Matthew Webb

Last, but not least, we have Daredevil Matthew Webb. This event dates way, way back to 1883.

As a professional swimmer, Webb wagered that he could swim across the whirlpool of the Niagara Falls. The bet was staked at $10,000 (a lot of money at that time). On July 24, 1883, Webb made his dive into the water – but then he was never to be seen again. One could say that this was the largest sports betting loss of all time.


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