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£100 on 2000/1 odds – Won £200,000

Leicester City’s 2015/16 Premier League title win came as a shock to everybody. While most football fans were more than happy to see the underdogs emerge victorious from what was a topsy-turvy season, bookmakers were left red-faced after offering odds of 5,000/1 against The Foxes before the campaign commenced. The blunder is said to have cost the bookies close to £20 million in won bets – the biggest ever single market payout in betting history. Had less people opted to cash-out for reduced profits, Leicester City’s triumph would have cost the bookmakers a whole lot more. One cool-headed punter, who chose to remain anonymous following his victory, did stick it out to the very end, winning a massive £200,000. Had they placed the bet at the start of the season, they would have bagged a cool half a million. However, the wager came in October, two months into the campaign when the bookmakers had (sort of) corrected their error and dropped the odds to 2000/1. Placing £100 on the unexpected victors was still a massive gamble, but ultimately one that paid off, as the anonymous punter emerged with one of the biggest payouts in betting history.

£2.50 on 108,800/1 – won £272,000

2011 got off to a flying start for one lucky punter, as he scooped a massive £272,000 from a £2.50 bet, which bookmakers Ladbrokes confirmed to be the largest payout in their history. The mystery better had placed a nine-match accumulator which successfully predicted underdog victories for the likes of Wolverhampton Wanderers and Blackburn Rovers, before concluding with a draw between Athletic Bilbao and Barcelona in the Copa del Rey Round of 16. Given Lionel Messi, Andres Iniesta and Xavi had just finished in first, second and third place for the 2010 FIFA Ballon d’Or award and Barcelona were cruising to the La Liga title, betting against the club sailing to yet another victory was extremely risky. With the game drawing to a close and Barcelona’ holding on to their 1-0 lead, the unfortunate punter’s hopes of a massive payout appeared to be all but over. That is, until Fernando Llorente popped up in the 85th minute to level the score. It didn’t change much for Bilbao, as Barcelona progressed to the quarter-finals on away goals, but it did make one spectator a quarter of a million pounds richer. 

30p at 1,666,666/1 odds – won £500,000

The 2000/01 season was decent enough for Manchester United, as they scooped their third consecutive Premier League title, which was also their seventh top flight title since the competition was rebranded in 1992, nine years earlier. The dominant club weren’t quite so lucky in Europe, as Germany giants Bayern Munich knocked them out of the Champions League at the quarter-finals stage. However, for one lucky Red Devils fan, Bayern’s progression made the season so much better. The unidentified fan had placed a 15-event accumulator in August 2000, before the season had kicked off. With a stake of just 30p, the punter didn’t appear to have much faith in the bet paying off, yet with odds of 1.66 million to one, not much of a wager was needed to generate one of the biggest football payouts of all time. Having correctly predicted the winners of the top five English leagues, three Scottish divisions, the Rugby Union champions and the cricket County Championship winners, it was down to Bayern Munich to win the Champions League and confirm the massive win. With the game going to penalties, it was one of few times that an Englishman was happy to see the Germans scoring from the spot.

80p on 683,738/1 odds – won £585,000

One lucky punter had one key rule in his betting strategy – never place a wager of more than €1 each time. All it took was one moment of luck for it to all pay off. The anonymous football fan from a small village in Malta has placed a 19-match accumulator via the William Hill website, with the final game to be played between Premier League rivals Chelsea and Liverpool. That weekend in November 2011 had gone largely as expected, with the favourites taking the spoils in the vast majority of the games played. With Chelsea favourites, things didn’t look good going into the match. Liverpool scored midway through the first-half, before Daniel Sturridge levelled following the break. The game appeared to be heading for a draw, until former-England right-back Glen Johnson popped up with three minutes left to play to score what proved to be a £585,000 goal. According to William Hill, the lucky victor wasn’t a Liverpool fan before kick-off, but he was by the time the final whistle was blown.

£100 on 6542/1 odds – won £650,000

Predicting eight match outcomes correctly is impressive, but predicting eight results while the games are already in play takes it to a whole new level. Some may call it stupidity, but it takes some guts to splash £100 on teams that are already losing, and for one lucky Londoner it certainly paid off, as he scooped the biggest payout in the history of the sport. The wager consisted of eight games which had just 20 minutes left to play, with many of the results going against his picks when it was placed. A draw for West Ham while they were 2-0 down to Stoke, Charlton to draw with Sheffield Wednesday in a game they were losing and the same for Coventry in their match against Leyton Orient. Having predicted a draw between Fulham and Wigan, the later went ahead with just eight minutes remaining and, with an extra man on the field, appeared likely to secure the victory – until Bryan Ruiz levelled from the spot with just two minutes to play to keep the hopeful punt alive. After a number of twists and turns it appeared likely that Coventry City, 2-1 down against Leyton orient, would be the only side to let him down – until Jim O’Brien struck in the 91st minute to confirm the draw and earn one ballsy better an unbelievable £650,000 – not a bad return for just 20 nerve-wracking minutes.