6 Devastating Sports Bets Where Gamblers Missed Out on Tons of Money

While some fans watch sports for the emotion and intensity, others add another dynamic — with their wallets. Sports gambling is a highly lucrative industry covering everything from on-field action to festivities surrounding the game.

One of the most popular ways for sports-watchers to make money is a parlay — a bet that hinges on a perfect combination of bets that increases exponentially with each new one. Unfortunately for this fan, one thing stood in the way: the Washington Redskins. 

1. A 20-team parlay?

The bettor paid just 89 cents on his parlay, but at 20 teams, his chances at hitting on the bet were murky, at best. Through 19 games, however, things looked good. He’d gotten every single bet correct. All he needed was a Redskins win over the Chicago Bears, and he’d be $500,000 richer.

Unfortunately, the Redskins are having a terrible season. After the team lost, it turned out to be a little more than a tragic story. This bettor wasn’t the only person to experience something like this. As long as there is betting, there will be more disappointment. These other people learned this the hard way.

2. Check the rules

In 2017, an English woman named Megan McCann sued Hillside (UK Sports) LP, a gambling company that runs bet365. Like the bettor who lost because of the Redskins, McCann did a parlay, although her bet was for £25,000. Another difference between that bettor and McCann is that McCann swept her parlay. Happy ending, right? Wrong.

Bet365 refused to honor the  £1,009,960 payout, claiming that she broke a “no third-party” rule by using the funds of others and accusing her of fraud. The case was discontinued in June 2019

3. A £1M Error 

A teen bettor in the United Kingdom named Jordan Donnellan correctly guessed the winners of 14 soccer matches on a similar parlay to some of the others. After celebrating with friends and getting ready for a payday, Donnellan tried to collect. However, he discovered he’d filled out the wrong form. Instead, he went home with nothing.

4. Pricing errors

At the Meadowlands Racetrack, a New Jersey man named Anthony Prince placed a $110 bet on a Denver Broncos game as they trailed with 70 seconds left. He won the bet and believed he deserved $82,610 in return. There was just one problem. FanDuel, the company he bet through, claimed there was a glitch that gave the wrong odds and refused to pay him.

5. A man barely misses a $100K payday

Those who are new to sports betting may wonder why many odds are done with “.5” on the end. This is to prevent washes. A man in Nevada learned this the hard way.

After getting the first 14 legs of a 15-leg parlay correct, the man just needed the Patriots to cover the spread so he could turn his $5 bet into $100,000. The New England Patriots won the game, but they failed to cover the spread by a single point. The man only had his hopes and dreams in the end.

6. Another man barely misses on $500K

One confident bettor put down $500,000 on the Cleveland Browns during Week 3 after buying the hype following them into the NFL season. All he needed was the Browns to cover the spread and he’d double his bet. Unfortunately, Cleveland lost him lots of money.