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Biggest Gambling Winners: The UK’s 5 Jammiest Punters


Fancy trying your luck at a sports betting site like bet365, but feel pessimistic about winning big? Well, the glass is very much half-full.

In fact, for some people, it’s positively overflowing. Dreams can come true, as any sports fan knows, and these are some of the UK’s biggest ever sports betting winners. Who’s to say you can’t follow in their footsteps?

Man U fan wins £157,000 from £2.50

This anonymous Manchester United fan was a regular at his local bookies in Lichfield. He was an unremarkable customer until, in 1999, he placed a £2.50 accumulator.

This included Manchester United to win the Champions’ League, which they memorably did (alongside the FA Cup and Premier League for a historic treble). When he collected his winnings, he told the shop he would be back to do it again – clearly not a man who quits while he’s ahead!

Leicester’s title gives bookies their biggest loss

When Leicester City won the 2015/16 Premier League, it was quite probably the most unpredictable upset in the history of football, or indeed all sport. At the start of the season, they were 5,000/1 – for reference, that was the same as the odds of Elvis Presley being spotted alive that year.

Diehard Leicester fans, or perhaps those who knew something we didn’t, netted up to £100,000 apiece when Tottenham Hotspurs’ draw in May completed the Vardy Party and won Leicester their title. On the other hand, UK bookmakers were less pleased at having to shell out over £25 million for their losses.

Eight horses, 50p, £1 million

Fred Craggs, from Yorkshire, is not a horse racing expert. He picked his eight-horse accumulator based on the names of the horses rather than any in-depth research.

That didn’t seem to matter for him, though: the horses Isn’t That Lucky, Racer Forever and A Dream Come True were a few of his eight winners on a 2,000,000/1 shot. That, for Craggs, was a sixtieth birthday to remember.

Frankie Dettori delivers for Darren

Darren Yeats from Morecambe, like many UK gambling fans, liked a bet on Ascot. He bet £59 that legendary jockey Frankie Dettori would win all seven races – a near-impossible feat.

Fortunately for both Dettori and Darren, the year was 1996 and that was the year Dettori did it. Yeats netted £550,000 back from his £59 investment.

Red Devil turns £0.30 into £500,000

Remember about five minutes ago, when you read about the Man U fan who turned £2.50 into £157,000 then cockily said he’d come back and do it again?

Well, he came back and did it again.

Two years later, another accumulator on a combination of rugby and football fixtures came through for him. When Bayern Munich bested Valencia in the Champions’ League final, it sealed the deal on a £500,000 win from just £0.30.

Since then, he doesn’t seem to have done it a third time – but we’re not holding our breath!