Top 10 Biggest Sports Bets Ever

As we lead up to Cheltenham, we thought it would be fun to look at 10 of the biggest sports bets ever.

The Cheltenham Festival is just around the corner. With the best horses in National Hunt racing competing for some of the biggest races in the sport, Cheltenham is about as good as it gets for punters.

Every punter loves getting one over on the bookies when it comes to Cheltenham.

For most of us, that means having a small bet for a bit of extra fun and entertainment but some people take their sports bets to a whole different level.

As we lead up to Cheltenham, we thought it would be fun to look at 10 of the biggest sports bets ever.

Cheltenham Freebets

Floyd Mayweather

Floyd Mayweather is the undisputed king of the ring. The legendary fighter ended his boxing career on 50-0 after outclassing Conor McGregor in arguably the most highly anticipated fight of all time.

Mayweather has never been shy of showing off the wealth he’s accumulated throughout his career and like many of us he loves a bet.

The difference between Floyd and us mere mortals is the amount of money he’s willing to risk. Just look at this picture of just one of his legendary bets. Could you guess he lives in Las Vegas?


I bet on @isaiahthomas today! ?? #TMT

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Billy Proves He’s the Best 

Floyd Mayweather loves the attention that his huge sports bets bring but don’t think he’s the best punter around.

For many, that title belongs to Billy Walters.

The legendary punter has made a series of huge bets throughout his life but perhaps the most famous is when he placed $3.5 million on New Orleans to win the 2010 Super Bowl.

The Saints were the underdogs but proved that Walters’ faith in them was well placed even though the exact payout he received is unknown.

Sadly for Walters, it all ended on a sour note when he was sentenced to five years in prison for insider trading.

An Unsafe Safety Bet

The Super Bowl has prompted thousands of people to make rather unwise betting decisions.

When Jona Rechnitz came up to the sportsbook at the MGM Grand in Las Vegas asking to bet $1,000 on the first score of Super Bowl XLVI coming via a safety, they almost laughed at him.

He had the last laugh though as the bet came in and he netted $50,000.

Ladbrokes Cheltenham free bet

World Cup Woes

Not every tale of a big money bet ends well.

Just ask the punter who staked over £400,000 on Germany beating Spain in the 2010 World Cup semi-final.

He got odds of 10/11 on the German’s proving their ruthless efficiency once again but was left devastated when Carles Puyol snatched a 74th minute winner to send Spain through to the final.

888Sport Cheltenham free bet

Golazo de Puyol - always remember! #2010worldcup #tbt

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Punter’s Generous Federer Gift 

It’s hard to imagine it now but there was a time when Roger Federer winning Wimbledon came as a surprise.

Few people backed the Swiss back in 2003 when he won his first title at SW19 but Nick Newlife was convinced enough by what he saw to place a bet of £1,520 on Federer winning six more Wimbledon titles.

Ladbrokes Non Runner Money back Cheltenham

Sadly, Mr Newlife died before he could collect his winnings of £101,840 but he donated his betting slip to Oxfam who benefited from his generosity and his ability to pick a winner.

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The Stable Lad’s Life Changing Punt

Horse racing connections often put their money where their mouth is and back their horses.

Conor Murphy, a stable lad at Nicky Henderson’s yard, knew more than most about the chances of Henderson’s best horses at the 2012 Cheltenham Festival.

Betfair NRNB Cheltenham Offer 2018

So he decided to place £50 on the five Henderson horses he rated as the best including Sprinter Sacre and Bobs Worth. And wouldn’t you know it, they all won giving Murphy more money than he’d ever seen before.

Frankie Sends the Bookies into a Tizz

Frankie Dettori is one of those jockeys who transcends horse racing.

The Italian is popular with people far beyond racing and his horses are always well backed as a result. He certainly had plenty of support back in 1996 when he went through the card at Ascot and won all seven races he was booked in.

The bookies took an absolute hammering that day but one lucky punter, Darren Yeats, took full advantage by winning over half a million pounds.

Fred Craggs’ Crazy Acca 

They say you have to speculate to accumulate but don’t tell lucky punter, Fred Craggs, that.

He placed a bet of just 50p on an eight-fold accumulator on horse races from Sandown, Wolverhampton and Dubai.

Whether Fred was just doing it for a bit of fun or was a master punter, we don’t know. What we do know is that he backed horses with names like Isn’t That Lucky and Dream Come True and that his 50p investment returned a cool £1 million.

Not bad ahead of his 60th birthday!

Paddy Power Cheltenham Offer

1,666,666/1 Madness 

Fred Craggs isn’t the only British punter to win a huge amount from a tiny bet.

Mick Gibbs, a roofer from the Staffordshire, only had a tiny amount to bet with but that didn’t stop him trying to win big by placing a 15-fold accumulator.

The 1,666,666/1 acca came down to Bayern Munich getting past Valencia in the Champions League. The Germans did so on penalites but it was Gibbs who was celebrating most as he scooped £500,000.

Go On My Son

There’s nothing like the love of a father to a son. Not only do they want the very best for their child, but fathers get the chance to live vicariously through the success of the son.

Gerry McIlroy has plenty of chances to enjoy the success of his son, Rory, on the golf course.

Long before McIlroy junior became the number one player in the world, Gerry and some friends showed they believed in his ability by betting £200 that he’d win the Open by the age of 25.

When Rory triumphed at Hoylake, Gerry and his mates collected at odds of 500/1.