We’ve all seen it, the smug Facebook post, or the retweeted betting slip with a huge profit from a tiny stake. Usually it’s “just” a few hundred dollars, but there have been some truly incredible bets down the years. There are a lot of similarities between betting on sports and actually playing sports. Luck is important, but ultimately you need skill to win consistently. The world of sport betting has its stars too. Some were very lucky, but most achieved their success through careful analysis and risk assessment. Here are 10 greatest and most memorable sports betting wins of all time.
The world’s biggest known accumulator win came in March 2011 in the UK, when plumbing engineer Steve Whiteley managed to win a staggering £1.45 million from a noble £2 bet. Whiteley, from Tawton in Devon, selected six winners on the Exeter Tote Jackpot from a choice of horse race meets across the UK and Ireland. His accumulator consisted of Semicolon (2/1), Black Phantom (12/1), Ammunition (16/1), Mr Bennett (16/1), Lundy Sky (5/1), and Lupita (12/1).
It does not come more perfect than 60-year-old fertilizer salesman Fred Craggs from Yorkshire, UK who won £1 million from a small 50p bet. Craggs placed an 8-fold accumulator with William Hill and his selections came from horse race meets scheduled across the globe. Bizarrely, Craggs was not even aware he had become a millionaire until he visited the same bookmaker to place another bet.
The UK might be renowned for its massive sports accumulator wins but the US can also deliver a big winner every now and again too. An anonymous punter from Las Vegas won $305,000 from a $5 parlay bet on a selection of basketball matches with William Hill back in March 2016. The punter backed a selection of college teams on the Saturday and Sunday, whilst also selecting NBA teams Detroit Pistons and Golden State Warriors to win on the Saturday. This left him needing Kansas to win on the Monday which they did. Boom.
November 2011 will remain one etched in the darkest reaches of the memories of UK bookmakers. It was a month when one weekend saw the vast number of favorites win their game leaving the bookies licking their wounds. The biggest payout was suffered by William Hill. A better living in a tiny village on the island of Malta placed an audacious 19-team accumulator. It was only an 80p bet. The better will forever be indebted to former Liverpool full back Glen Johnson who bagged a winning goal 3 minutes from time to seal a win for the Reds against Chelsea and deliver the six-figure win for the lucky bet placer.
The odds are often skewed by passionate fans who’ll bet on their team no matter what. Sometimes, it pays off for them though. In 2011, one anonymous baseball fan bet $250 that the St. Louis Cardinals would make the World Series at odds of 500. This person then bet another $125 that they would win the World Series at 999 in odds. The Cardinals hardly looked impressive at the time of the bet, but soon started winning games at a surprisingly consistent rate. They ended the year as the most unlikely World Series champions and the fan picked up $375,000 in return for his faith.
28 September 1996 was an infamous day at Ascot racecourse in England. Franki Dettori was a popular jockey and a favorite with many punters, although one person who didn’t agree about his chances that day was Dettori himself. Interviewed before the first of his seven races, Dettori said that it was possible he could maybe win two of them. Many punters bet on Dettori anyway, including Darren Yates who put down £67.58 and decided to combine all seven of his races into a single bet that Dettori would win them all. Yates was a struggling businessman with a small carpentry business so needed a change of fortune. After place the bet, Dettori went off to play football with his friends and lost the game 4–0. Thinking it wasn’t his day, he then went to check on Dettori’s races and discovered that Dettori had won all seven. There were many winners that day at Ascot but no one earned more than Yates who picked up £550,823.
Mick Gibbs is a roofer by profession, constructing and repairing roofs across Staffordshire in England. That’s not his only skill however. Gibbs also has an eye for winning accumulator bets. His first big win came in 1999 when he bet £2.50 and correctly predicted nine football games across Europe. That earned him £157,000. That’s small change compared to his next big win however. In 2001, Gibbs bet 30 pence to predict the winners of 15 football games across Europe and was given odds of 1,666,666. The first 14 games went exactly as Gibbs predicted so everything now depended on a Champions League match in which Bayern Munich would need to beat Valencia. The game ended in penalties. The last kick of the game was from Valencia defender Mauricio Pellegrino, but the moment the ball landed in the hands of Bayern Munich’s goalkeeper, Gibbs was £500,000 richer. Not bad for a 30 pence stake.
Horse racing was once again the sport of choice for one anonymous punter who secured an £823,000 win from a £19 accumulator bet. The odds were high but the larger bet stake allowed the individual to win such a high amount. The lucky winner was from the UK county of Leicestershire and bet on a 5-fold from a selection of horse racing meets back in April of this year. The bet remains the largest ever win paid out by bookmaker Coral.
26 year old Tayla Polia placed an outrageous 15-team parlay on a selection of NFL games at odds of 20,000/1. Her bet included Vikings -5, Falcons +3, Texans +1, Chiefs -8, Redskins +1, Patriots -14, Cardinals -4, Giants +5, Seahawks -14, Packers -3, Chargers -2, Steelers -6, Steelers/ Broncos over 45, Bengals -4, and Lions +3. She guessed them all correctly and won $100,0000. It might not be the biggest win in terms of money but it certainly is one of the biggest in terms of sheer guts judging by the selections made.
Bill Walters used to be a professional poker player before using his skills as a professional sports punter instead. Over nearly four decades, Walters has bet more money than anyone else in history and continued a winning streak that has earned him hundreds of millions of dollars. He’s living proof that sport betting is a game of skill. Like poker, Walters explains that winning sports punters have to analyze information then calculate risk and potential profits. In an interview with CBS News, Walters described his biggest and most audacious bet of all time. The New Orleans Saints were playing the Indianapolis Colts at the Super Bowl in 2010 and the consensus was that New Orleans were the underdogs. Walters analyzed all the information he had and discovered that it actually favored New Orleans as the most likely winners. He looked at the odds, calculated the risk and potential profit then decided to bet big. Walters bet $3.5 million on the supposed underdogs and New Orleans didn’t let him down. They defeated the colts 31–17 to win their first ever Super Bowl.
How much did Bill win?
No one knows, but given that the Saints were the underdogs, we’re sure he made a pretty penny off this single bet.
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