The Biggest Sports Betting Wins Of All Time

1 year ago

All of us dream of one day winning an enormous bet, but very few ever manage it. Then again, when do many of us have the opportunity to even have a sniff at getting our hands on a life-changing sum of money?

Even with the most improbable of odds, we debate what we would do if our ridiculous gamble paid off. Would we still turn up at work the next day? Or instead, would we travel the world, buy a mansion; invest for the future, or even all three?

Once in a remarkable while, there is someone out there either touched by genius or madness and defies all the odds in a spectacular way. Here are a selection of those unexpected winners that left a sizeable hole in the pocket of the bookmakers and illustrated that the impossible is, just sometimes, possible.

Horse Racing

£2 on 725,000/1 – £1.45 Million Win

Plumbing engineer Steve Whiteley landed himself in betting folklore as he scooped a cool £1.45 million from a humble £2 bet. Whiteley chose six winners on the Exeter Tote Jackpot from a variety 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). As destiny would have it, the jockey (Jessica Lodge) that clinched the jackpot by riding Lupida to glory had never tasted success in 28 previous attempts – so as the saying goes, when your luck’s in, your luck’s in.

50p on 2,000,000/1 – £1 Million Win

This classic rags to riches tale saw 60-year-old fertilizer salesman Fred Craggs’ wealth and fame grow to new heights as his 8-fold accumulator with William Hill in 2008 landed him £1 million from a rather modest 50p bet.

With a smudge of irony, the first race’s winning horse was named Isn’t That Lucky, and the final horse that won the eighth race bore the name A Dream Come True.

The modest Yorkshireman was not even aware he had become a millionaire until he visited the same bookmaker to place another bet. Clearly shocked and taken aback, Craggs himself admitted: “I’ve never spent more than the price of a packet of cigarettes on a bet, so it is very surprising that I won this much money.”


£100 On 6542/1 Odds – Won £650,000

In just 20 nerve-jangling minutes, an anonymous bettor from London turned £100 into a staggering £650,000 after correctly predicting eight results whilst the games were still in progress.

The lucky Londoner placed his stake on teams that were already behind, with Charlton and Coventry one goal down to Sheffield Wednesday and Leyton Orient respectively – whilst West Ham trailed by two goals to Stoke at the Britannia Stadium. After a number of twists and turns, it was Jim O’Brien that levelled for Coventry in the 91st minute to turn this hopeful punt into a magical reality.

Some may label it stupidity, but placing £100 on losing teams takes guts. To date, it remains the biggest payout in the history of the sport.


£1,520 on 66/1 Odds – Won £101,840

There is no doubt that tennis fan Nick Newlife was impressed with Roger Federer’s performance in claiming his first Wimbledon victory 14 years ago – so impressed that he predicted the Swiss star would go on to equal the record of seven SW19 crowns alongside William Renshaw and Pete Sampras.

Unfortunately, Newlife never saw his prediction come to fruition as he passed away three years before Federer’s four set triumph over Andy Murray in 2012. Luckily, the benovelent man from Tackley, Oxon left the betting slip in his will to the charity Oxfam who benefitted from the winnings instead.

Newlife clearly had an eye for talent – this season a rejuvenated Federer elevated his Grand Slam tally to 19, including becoming the first man in history to win eight Wimbledon titles.


Written by Oli Coates

Oli Coates is a huge sports fan, particularly football and especially Manchester United, who follows sports betting closely and has written extensively on the market. An experienced writer, Oli has covered everything from travel to how to care for your pets!