Best sporting wagers between celebrities and sports stars

Everyone that has seen the highly entertaining snooker shootout match-up between West Ham United duo Andy Carroll and Carl Jenkinson will know that much was at stake in their battle on the baize.

As part of a connection with Betway and the Hammers, who are currently flying high in the Premier League this season, both east London stars came face-to-face on the green cloth for a snooker match.

Both Carroll and Jenkinson were trained by potting professionals Judd Trump and reigning world champion Stuart Bingham in a bid to outpot each other, with the loser having had to clean the victor’s boots.

Following the hugely enjoyable snooker video, it’s got people thinking of other friendly wagers which high-profile sports and famous celebrities have been involved in, though only legal ones of course!

The losing temporary cueist from Carroll and Jenkinson’s shootout was obligated to clean the winner’s football boots, but in many other scenarios, friendly wages between some of the biggest stars in the world have involved a lot higher stakes.

Oscar De La Hoya v Jay Z

For the WBC middleweight showdown in Las Vegas between defending champion and four-division title winner Miguel Cotto and his Mexican challenger Saul ‘Canelo’ Alvarez, there was quite a hefty sum placed between two other global superstars.

This Nevada meeting is just the latest chapter of a long-standing boxing rivalry between fighters bearing from Mexico, and those coming from neighbours Puerto Rico, as Cotto and Canelo clash in the ring.

With so much on the line within the squared circle, outside of it there is just as much, or arguably more, with two of the bout’s main promoters going against each other in a mammoth friendly wager.

Former six-division world champion Oscar De La Hoya, now Golden Boy promoter, has an enormous $100k wager with Roc Nation promoter and American rap star Jay Z, with the money resting on the outcome of Cotto versus Canelo.

The loser of this gigantic bet will have to donate that substantial amount to a charity of the winner’s choosing, with De La Hoya on his young Mexican fighter Canelo’s side, while Jay Z is in the corner of Puerto Rican champion Cotto.

This fight is one of the most anticipated of the year, as Cotto defends his WBC strap for the second time. His maiden defence came against Daniel Geale in June, as he dominated the bout to triumph with a fourth-round TKO, having won his belt from Sergio Martinez earlier this year.

Canelo comes into the high stakes match-up on the back of a thunderous knockout of James Kirkland in the third round of their meeting in May. The Mexican bruiser makes his first attempt at claiming the middleweight belt, having previously held the WBC and WBA super-welterweight straps, before losing them to Floyd Mayweather Jr in 2013.

De La Hoya, who defeated 17 world champions and won ten world titles during his fighting career, will hope his young prodigy Canelo can win his chosen charity some funds, while Jay Z will be spurring on Cotto in this friendly, yet substantial wager between two global stars.

Paddy McGuinness v Emile Heskey

Elsewhere in the world of sport, there have been other bets between familiar faces, with much-adored comedian and TV presenter Paddy McGuinness raising the stakes against footballing cult hero Emile Heskey this year.

McGuinness, a passionate Bolton Wanderers fan, tweeted in 2014: ‘If @EmileHeskeyUK comes off the bench today and scores for us I’ll personally clean his boots! C’mon Bolton!!!!’

Tweeting in regards to former Liverpool striker Heskey’s switch to Bolton last year, the comedian was another to raise those high stakes of cleaning dirty boots, something which he lived up to in the New Year.

Heskey did indeed manage to strike past Blackburn Rovers on Boxing Day, netting the equaliser against their Championship rivals in an eventual 2-1 victory for McGuinness’ supported side.

Therefore, for the Take Me Out host, it was a case of, let the brush see the boot at Bolton’s training ground, as he was true to his word, after losing his bet.

Mark Wahlberg v P Diddy

Back to the financial high stakes with this friendly wager between American actor Mark Wahlberg and famous rapper Sean Combs, aka P Diddy.

Ahead of last summer’s highest ever grossing boxing match-up featuring ‘Money’ Mayweather and Manny Pacquiao, these two celebrities entered into a huge bet against each other.

Diddy announced before the fight that he was putting his money where his mouth was and staking $250k against Wahlberg in favour of his friend Mayweather overcoming Pacquiao, which, of course, he did in the end.

The rap star posted a video on his Instagram account confirming such a wager took place, with him and his Hollywood actor ally toasting their wager in front of a swimming pool, but it was Wahlberg’s money that was soaked up by Diddy in the end.

6 thoughts on “Best sporting wagers between celebrities and sports stars

  1. Pocket change for these guys…that’s like me dropping a hundy on Chris aka SC at the bar to make sure the girl I’m hitting on always has a fresh drink.

  2. Anticipate fight of the year turned out to be a joke . Cotto is way past his prime . Alvarez will have his @ss handed to him by Gennady Golovkin should they ever meet in a boxing ring.

    Nothing like having a former drug dealer (Jay-z) and cocaine user (de La Hoya , known cross dresser) wagering a bet on a title bout .

  3. Maybe it is the time of year talking here but you would always hope if these 1 percenters want to make a whacked wager the winnings would wind up in a charity instead of their pockets…as it is truly pocket change for them all.

  4. Pingback: Football face-offs - Football Betting

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