Against All Odds: Biggest Betting Upsets of All Time

On a regular day in the sporting calendar, the bookies are guaranteed to turn a tidy profit from their customers. But every so often one extremely lucky – or clever – gambler manages to beat the odds and walk away with a huge sum of money from an unlikely bet. Here are some of the betting upsets that have gone down in infamy.

Gino DiFelice and the Fail Mary

In 2012, Canadian Gino DiFelice was waiting on the outcome of the clash between the Green Bay Packers and the Seattle Seahawks. Having already predicted the outcomes of 14 other NFL games correctly, this final result was all that was standing between him and a staggering win.

The game went down to the wire, and was ultimately decided by a controversial Hail Mary pass that handed the game to the Seahawks by the narrowest of margins. The incident famously became known as the ‘Fail Mary’, as the official’s decision to award the touchdown was dubious at best. Good news for DiFelice, who received the full $725,000 from his original $5 bet.

Leicester City Top the English Premier League

One of the most popular sporting leagues in the world, the EPL is not usually full of big surprises. Teams that receive a massive injection of cash may be expected to up their game fairly rapidly, but aside from that the final top ten are generally a mix of the usual suspects.

The bookies were caught out in a big way in the 2015/16 season, when rank outsiders Leicester City rocketed up the table and proved unstoppable. During the previous season the team had faced relegation fears, ultimately finishing in fourteenth place. At the start of the next season, their odds for topping the table were set at 5,000-1. Only 24 people made the bet before the first kickoff. By the time Leicester lifted the trophy, UK bookies had paid out more than $34.5 million.

Overnight Millionaire

A horse racing fan from Yorkshire in the UK received the best birthday present imaginable in 2008 when he became a millionaire overnight – from a stake of just fifty pence (around $0.70). Fred Craggs placed the eight-race accumulator bet as a bit of fun, and didn’t even check the ticket at first.

Only when he next visited the bookmaker, to place some more small bets, was he informed that the 2,800,000-1 odds had netted him a million pounds sterling. At the time, this was the maximum payout for horse racing, and Craggs was the first customer ever to win it. Fittingly, the name of the first horse was Isn't That Lucky, and the last was A Dream Come True.
World Series Wild Cards
In 2011, the St Louis Cardinals were a Major League Baseball wild card team. The chances of them even making the playoffs had been looking slim, so the odds stayed high for them to be the eventual winners. One devoted fan had enough faith to place a $125 bet at 999-1.

Going up against defending American League champions the Texas Rangers, the Cardinals played a nailbiter for the seven games of the World Series. Tied after the sixth game, the Cards pulled it out of the bag to score the title in the final clash. After a season dogged by injury and the loss of some key players, the bookies were likely surprised that they had to cough up the cash.

Kentucky Derby Makes the Headlines

It may be a household name today, but back in 1913 the Kentucky Derby was not yet on many people’s radar. The result that year, the 39th running of the annual race, cemented its place as a premier sporting event in the American calendar. Donerail was the winning horse, a locally-reared thoroughbred who still to this day holds the record for the longest odds victory in the history of the race.

At 91-1, Donerail was clearly not seen as a threat. Jockey Roscoe Goose held the stallion back until the home stretch, but when he was unleashed he forged ahead to overtake the three in front and win over favorite Ten Point by half a length. Although his time doesn’t even make the top fifty today, Donerail set the record that day. From a bet of just $2, one lucky racegoer received $184.90 – which translates to almost $5,000 in today’s money.

The Ultimate Beginner’s Luck

In 2015, Las Vegas resident Tayla Polia was trying to learn how spread betting works. As she recalls, her boyfriend was getting frustrated with explaining it, so she decided to learn by doing and try it out on the day’s NFL games. Polia knew that the parlay bet she placed on all 15 fixtures was ludicrous, but it wasn’t really about winning.

Imagine her surprise when all her bets came through. Polia won a cool hundred grand after betting just $5, beating the 20,000-1 odds.

If You Win, Make Sure The Payout is Fast

There you have it, some of the biggest upsets that have cost bookmakers a lot, or have brough piles of money to the winners. While these situations are rare, everyday people do win by gambling – either in sports or in online casinos. These winnings will be taxed depending on their country of residence. Example, in Germany taxes will probably higher than in the Finland where gambling is tax free. Sometimes there are issues with payouts for simple reasons that all documents aren’t in order or that casinos/bookies suspect irregularities. When all the procedural red tape is cleared, transfers of money can also take a while, depending on the amount. In order to speed things up, punters should always consider using quick withdrawal operators which guarantee short processing periods and generous payout terms. Keep this in mind, just in case you win big and don’t want to wait too long.