Cheltenham 2022

Cheltenham Top 5′s: Five Cheltenham Winning Gambles


The Cheltenham Festival is one of great British sporting spectacles with the same horses returning year after year to do battle for top prizes at the fabled ‘Home of National Hunt Racing’. We’re providing Cheltenham Betting Offers each year so please check our pages regularly.

For the average Joe though it’s all about the betting action, and everyone loves landing a big Cheltenham winner, or putting together a speculative Yankee bet with your four Cheltenham bankers.

But what are the biggest ever punts ever landed at the Festival. Here’s five of the best moments when the ‘old enemy’ (the bookmaker) was well and truly clobbered!

1. Destriero – 1991 Supreme Novices Hurdle

As Cheltenham gambles go, Destriero winning the opening race in 1991 has to be right up there.

He was owned by JJ Furlong, an Irish carpet manufacturer known as ‘Noel’ (because he was born on Christmas Day), who later went on to win the 1999 World Series of Poker main event and collected a £1.5 million prize.

Destriero had only raced twice and was a big odds outsider and was largely unconsidered. Still available at 16/1 shortly before the off, the cash then started to pour in for the 5-year old. His odds were just 6/1 when the tapes went up.

This masterplan was carried out with clinical precision with Furlong managing to get £300,000 onto his horse and the result never looked in doubt. He beat Granville Again by 4 lengths up the Cheltenham hill.

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2. Forgive n’ Forget – 1983 Coral Golden Handicap Hurdle

Legendary Irish gambler, racehorse owner and trainer Barney Curley had a hand in one of the biggest Cheltenham coups of all time.

He sold a horse by the name of Forgive n’ Forget who is best remembered for winning the Cheltenham Gold Cup in 1985 but two years earlier he lined up as 5/2 favourite in a 23-runner handicap that is now known as the Pertemps Hurdle.

The horses new trainer Jimmy Fitzgerald knew how good the horse was, as did connections and their horse was duly backed at all double-digit prices from the moment the weights were announced.

He romped home under a confident ride from 19-year old Mark Dwyer coming from behind to defy his 11st-6lb weight.


3. Kicking King – 2005 Cheltenham Gold Cup

After Kicking King won the King George in 2004 and went into the Gold Cup betting at odds of 6/1 but after a poor scope in early March showed an infection and it looked as if he would not be fit enough to race.

The Betfair betting exchange reacted to this news by pushing his odds right out to 999/1 where a total of £94 was matched. Just a week later his odds were back in to odds of 14/1 and following the news that his connections had decided to let nature take its course and not use antibiotics his price tumbled even further.

Once Best Mate was withdrawn his price collapsed and Kicking King went off 4/1 and ran out a very impressive winner leaving two Betfair customers very happy with their bets – one had a £25 bet to win £25,000 and another placed a £10 bet to collect £10,000.

Interestingly, five years later the same thing happened – another apparent ‘non-runner’ Binocular gets laid at odds of 999/1 on Betfair.


4. Unsinkable Boxer – 1998 Unicorn Homes Hurdle

The genius that was Martin Pipe galvanised the 9-year old Unsinkable Boxer to win what is known as the Pertemps Hurdle. The same race won by Forgive n’ Forget 15 years earlier.

The horse was unexposed but looked fairly ordinary but Pipe transformed this horse and took him up to a new level winning three races and going up 34lb in the handicap in the process.

Pipe knew he had something special on his hand and even went as far to say publicly that his horse was “the biggest certainty to set foot on Cheltenham racecourse”.

Going off the 5/2 favourite against 23 rivals he won doing handstands (4 lengths officially) with Sir Anthony McCoy doing the steering.


5.) Conor Murphy – £50 Winning Acca Bet in 2012

It was a case of good news and bad news for 31-year old stable-hand Conor Murphy landed an outrageous £50 accumulator bet on 5 of his bosses horses. (Nicky Henderson)

The good news was that all 5 horses won however the ‘bad news’ was that the bookmaker had a payout limit of £1m. His actual bet winnings came to £3.1m but he was ‘only’ paid £1m.

Murphy who placed the bet before Christmas was nevertheless delighted with his 5 winning horses being:

  • Sprinter Sacre (Arkle Trophy) (6/1)
  • Simonsig (Neptune Hurdle) (12/1)
  • Bob’s Worth (RSA Chase) (6/1)
  • Finian’s Rainbow (Champion Chase) (8/1)
  • Riverside Theatre (10/1)

His final selection Riverside Theatre, who was owned by the actor James Nesbitt, jumped the last in second place behind Albertas Run but a rousing finish from jockey Barry Geraghty had the whole place on its feet to cheer the monster bet home by half a length.

Conor Murphy invested his winnings wisely and went on to become a successful racehorse trainer himself in the USA.