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The XI Biggest Gamblers in Football

Footballers are notorious for high stakes gambling habits. Check out the Jackpot Gambler's XI to find out which players are making the most extravagant bets who has accumulated the biggest losses.


4 Dec 2014

The words football and moderation go together like Mourinho and modesty, like Heskey and clinical or Rooney and articulate.

The ultra-professional footballers of today have largely turned their back on drink and drugs, instead opting for the more glamorous, yet equally damaging, vice of high stakes gambling. Hyper-inflated wages have unsurprisingly led to gambling debts in the millions for some footballers.

At Jackpot.co.uk, we’ve put together a guide to the biggest known gamblers in the game, including high profile cases as well as those who’ve slipped under the radar. Read and share our Gambler’s XI and leave us a comment if you think we’ve missed anyone.


Roy Carroll

Roy Carroll
Estimated losses: £30,000+

Credit: Martin Rickett/PA


Kenny Sansom

Kenny Sansom
Estimated losses: £1 million+

Credit: Rex

  • Clubs: Arsenal, Crystal Palace, QPR
  • Game of choice: Sports betting, horses
  • Moment of madness: After spending all of his career earnings in the bookies and down the pub, ex-England and Arsenal defender, Sansom was found to be living on a park bench in Bromley.
  • Biggest loss: After his wife won £800 playing Bingo, Sansom took her winnings and bet it all on a single horse. Sansom’s wild bet didn’t come off and he and his wife are now divorced.
  • Last seen: Working as a scaffolder to keep him out of the bookies and off the bottle.

Dominic Matteo

Dominic Matteo
Estimated losses: £1 million

Credit: Sky

  • Clubs: Liverpool, Leeds
  • Game of choice: Horses
  • Moment of madness: At the height of his gambling habit, Matteo put a £200,000 bet on a single horse. Luckily, for him, the horse won.
  • Biggest loss: Not content with his winnings from the £200,000 bet, Matteo put another £100,000 bet on a horsed priced at evens but this time he wasn’t so lucky.
  • Last seen: Applying to be the next Leeds manager, more commonly known as the musical chairs of football management.

Tom Williams

Tom Williams
Estimated losses: £900,000

Credit: Mirror

  • Clubs: Guildford City, Peterborough United
  • Game of choice: Horses, sports betting
  • Moment of madness: Williams maintained a secret £30,000 per week gambling habit, betting while his wife and two children were asleep. His addiction came back to bite him when bailiffs turned up at his Buckinghamshire home demanding £900,000 in accumulated debts.
  • Biggest loss: Divorcing his glamour model wife Nicola Maclean
  • Last seen: Running away from a mediocre football career to live in Vegas…not the best of life choices if you’re a gambling addict.


Matthew Etherington

Matthew Etherington
Estimated losses: £1.5 million

Credit: Planetf1

  • Clubs: Stoke, West Ham
  • Game of choice: Poker, horses, dogs
  • Moment of madness: Etherington would regularly bet his weekly wages (£20,000) on the team bus to matches while at West Ham.
  • Biggest loss: Etherington accumulated losses of £1.5m, turning to loan sharks to fuel his habit. Eventually Stoke manager Tony Pulis stepped in and set him on the road to recovery.
  • Last seen: Sitting by the phone, waiting to be recalled to the Stoke team.

Paul Merson

Paul Merson
Estimated losses: £7 million

Credit: Sky

  • Clubs: Arsenal, Aston Villa, Portsmouth
  • Game of choice: Anything and everything
  • Moment of madness: On one night of a 10 month drug binge, Merson bet £10,000 on the Eurovision song contest, £5,000 on a bowls match and £2,000 on an NFL game.
  • Biggest loss: In 2008, Merson gambled away his £300,000 flat and was forced to move back into his parent’s house.
  • Last seen: Struggling to string a sentence together on Soccer Saturday.

Dietmar Hamann

Dietmar Hamann
Estimated losses: £600,000+

Credit: AFP

  • Clubs: Liverpool, Bayern Munich, Manchester City
  • Game of choice: Sports betting
  • Moment of madness: In 2009, a spread betting firm filed papers with the High court, after Hamann failed to keep up with repayments on his £600,000 gambling debt.
  • Biggest loss: Hamann put a spread bet on a cricket match, buying Australia for £2,800 at 340 runs. So for every run over 340, Hamann would win £2,800 and he would lose the same amount for every run under. Australia were bowled out for 237, meaning that Hamann lost a hefty £288,400 on a single bet. Hamann recalls, “Every wicket felt like a stab in the heart.”
  • Last seen: Being called a “skint knobhead” by Joey Barton on Twitter.

Keith Gillespie

Keith Gillespie
Estimated losses: £8 million

Credit: Getty

  • Clubs: Newcastle, Manchester United, Sheffield United
  • Game of choice: Sports betting, horses, dogs
  • Moment of madness: While at Newcastle, Gillespie placed a £500 bet on a game he was playing in. Newcastle won the game, but Gillespie’s bet didn’t come off, meaning he lost out on over £40k.
  • Biggest loss: In 1995, Gillespie frittered away a year’s worth of wages (£62,000) on the horses in less than 48 hours.
  • Last seen: Flogging his autobiography in an attempt to make back some of his losses.


Wayne Rooney

Wayne Rooney
Estimated losses: £765,000+

Credit: INFphoto

  • Clubs: Manchester United, Everton
  • Game of choice: Blackjack, roulette, horses
  • Moment of madness: Gambled away £65,000 within two hours of entering Manchester235 Casino
  • Biggest loss: Back in 2006, 20 year old Rooney, allegedly fell out with some fellow England teammates over a £700,000 gambling debt just before England’s failed World Cup campaign in Germany.
  • Last seen: Losing at the blackjack table and throwing a tantrum after realising that he won’t be able to pay for his next hair transplant session.

Eidur Gudjohnsen

Eidur Gudjohnsen
Estimated losses: €9 million

Credit: Planetf1

  • Clubs: Chelsea, Barcelona, Tottenham
  • Game of choice: Casino games
  • Moment of madness: After revealing the full extent of his gambling problem to the world, Gudjohnsen moved from Barcelona to Monaco, presumably to hit up the Monte Carlo Casino…not the smartest of moves.
  • Biggest loss: Back in 2003, Gudjohnsen opened up to the press revealing that he had won £100k at a casino and then, in the same night had gone on to lose nearly £500k.
  • Last seen: Training with relegation contenders Bolton Wanderers.

Michael Chopra

Michael Chopra
Estimated losses: £2 million

Credit: Reuters

  • Clubs: Newcastle, Ipswich Town, Cardiff City
  • Game of choice: Sports betting, cards
  • Moment of madness: In 2011, loan sharks came to the Ipswich training ground threatening Chopra to pay up on his gambling debts.
  • Biggest loss: Chopra and Newcastle teammates would bet up to £30,000 a time on card games while on the team bus.
  • Last seen: Renouncing his British citizenship to play for India.


Steve Claridge

Steve Claridge
Estimated losses: £400,000+

Credit: PA

  • Clubs: It’s probably easier to list the teams Claridge hasn’t played for.
  • Game of choice: Sports betting, horses
  • Moment of madness: Claridge was known to have £5,000 stuffed in his tracksuit, so he could head straight to the bookies after training.
  • Biggest loss: Claridge once lost £3,000 to manager Barry Fry on the way to a game and was left with £3.19 in his pay packet after his debts had been deducted.
  • Last seen: Shouting his half-baked opinions as a pundit on the BBC.


Teddy Sheringham

Teddy Sheringham
Estimated winnings: £206,000+

Credit: PA

  • Clubs: Tottenham, Manchester United, West Ham
  • Game of choice: Poker
  • Moment of genius: Poker ace Sheringham made the final table in the EPT Vilamoura tournament in 2010, winning a whopping €93,000.
  • Biggest loss: Splitting up with glamour model ex-girlfriend Danielle Lloyd
  • Last seen: Working his magic away from the poker table and back at the training ground. Sheringham has helped turn West Ham’s fortunes around in the league this season working as an attacking coach.

Jimmy Nielsen

Jimmy Nielsen
Estimated losses: $250,000+

Credit: ISIphotos

  • Clubs: Sporting Kansas City
  • Game of choice: Casino, sports betting
  • Moment of madness: At the height of his gambling addiction Nielsen walked into a casino and defied the odds to win $500,000. Not content with his winnings, Nielsen, also known as the White Puma, returned to the same casino the next day and gambled away $350,000 of his winnings.
  • Biggest loss: Nielsen couldn’t keep up with his repayments in 2004, after accumulating gambling debts of over $250,000 and caused a local bookmaker to close down. Nielsen also used his wife’s credit card to go on a casino spree in Las Vegas.
  • Last seen: Struggling to adapt to life as an ex-pro

David Bentley

David Bentley
Estimated losses: £1 million+

Credit: Mirror

Gamblers XI