Cheltenham Festival: Five Biggest Cheltenham Gambles

Updated: 28/02/2024

Richard Marsh | 15 January 2019

The Cheltenham Festival is renowned for the huge wagers staked and massive horse racing gambles attempted.

It’s also famous for the annual battle between bookies and punters.  Usually, Cheltenham Festival punters want favourites to win. That normally means doubles, trebles, four-folds and more are won, and the bookies are the losers.

But sometimes, the odds-makers can be smashed by the biggest Cheltenham gambles. They’re the Cheltenham Festival results the bookie didn’t see coming.

It’s happened a fair few times over the years, including the famous Unsinkable Boxer in 1998. Here are five punts which hit Coral hard:

Son Of Flicka – 2012 Coral Cup

Son Of Flicka landed an almighty touch for connections when bouncing back to form to land the Coral Cup in 2012.

The Donald McCain trained gelding was on a losing run of 11 heading into the 2m 5f contest but had run well to finish runner-up at the Festival 12 months earlier and been given a chance by the handicapper.

Having been as big as 66/1 on the morning of the race, the eight-year-old was backed at all rates down to 16/1 come flagfall.
Son Of Flicka raced prominently throughout in the 28-runner contest and stayed on strongly after the last under a positive ride from Jason.

Maguire to win going away by 3 1/2 lengths from Get Me Out Of Here.

Owner Phil Williams landed £900,000 with bets of his own, and others connected to the stable also bagged huge sums.

Son Of Flicka didn’t win again for over three years, but he delivered on the day when the money was down and that was all that mattered.

Xenophon – 2003 Coral Cup


Irish trainer Tony Martin has long been associated with pulling off major gambles, and the one on Xenophon in the Coral Cup hit the sponsors for six.

Having been backed down from 20/1 ante-post, Xenophon opened up at 8/1 with Coral on the morning of the race before being hammered down to 4/1 favourite come the off.

The Martin money was down and jockey Mick Fitgerald had the task of keeping Xenophon out of trouble in the huge 27-runner field before hopefully producing him late to land the spoils.

Fitgerald was coolness personified in the race, and after closing on the leaders two from home Xenophon only had to be shaken up to lead at the last before being driven clear to score by a cosy 3 1/2 lengths.

The gamble had been landed with ease in what is traditionally one of the most competitive races of the Festival, and the roar of the crowd as Xenephon and connections returned to the winners’ enclosure suggested the vast majority of racegoers had put their trust in Martin’s renowned skills off getting one ready to land a punt.

Unsinkable Boxer – 1998 Pertemps Final


Legendary trainer Martin Pipe pulled-off a number of gambles at the Cheltenham Festival during his illustrious career, and Unsinkable Boxer was one of the biggest when running out the facile winner of the ultra-competitive Pertemps Final.

The nine-year-old had looked very ordinary before joining Pipe, but his new handler quickly transformed him.

Unsinkable Boxer won in a good style of his first three starts in novice hurdles and was allotted an opening handicap mark of 136.

Pipe knew he was much better than that and is rumoured to have told champion jockey AP McCoy “this is the biggest certainty that you will ever ride” as he legged him up in the parade ring before the 24-runner contest.

That confidence was reflected in the betting ring as Unsinkable Boxer was backed as if defeat was out of the question and sent off the 5/2 favourite.

His backers never had an anxious moment as McCoy brought him from off the pace to lead on the bit two from home and win in a canter by four lengths from Tompetoo.

Destriero – 1991 Supreme Novices’ Hurdle


Destriero landed one of the greatest gambles of the modern era in the 1991 Supreme Novices’ Hurdle at the Cheltenham Festival when storming clear to beat Granville Again by four lengths.

The gelding was owned by World Series of Poker winner and Irish businessman Noel Furlong, who claimed to have netted more than £2m with his perfectly executed coup.

Furlong had an army of accomplices placing bets in different shops to mask the gamble, and revealed after the success that he had decided not to run Destriero again after he had made a winning debut over hurdles at Leopardstown on Boxing Day “as we didn’t want to end up getting 2/1 instead of 6/1”.

It could have been worse as Furlong had Destriero in a ruck of doubles with another of his horses, The Iliad. But that one made a bad mistake, which put paid to his chances in the Champion Hurdle and saw him trail in a distant 21 of 24 behind Morely Street.

Forgive n’ Forget 1983 Coral Golden Hurdle Final


Forgive n’ Forget is best known for winning the Gold Cup in 1985, but for punters, his greatest moment came when landing an almighty plunge in the 1983 Coral Golden Hurdle Final.

The horse had been purchased by Tim Kilroe from renowned gambler Barney Curley, and he hatched a plan with trainer Jimmy Fitzgerald to give the bookies caning in the race now known as the Pertemps.

Forgive n’ Forget was backed at fancy double-figure odds as soon as the weights were revealed, and that support continued on race day and saw the gelding sent off the 5/2 favourite for the 23-runner contest.

In the race itself, there was never any doubt that the gamble would be landed.

Jockey Mark Dwyer oozed confidence throughout, and after making smooth headway from the rear Forgive n’ Forget was produced to take up the running at the final flight before scooting clear to easily beat Brunton Park and land connections an estimated £1m pay-out.


This post first appeared here

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