cheltenham racecourse - The Biggest Gambles That Paid Off At Cheltenham Racecourse

The Biggest Gambles That Paid Off At Cheltenham Racecourse

Cheltenham racecourse is the home of national hunt racing and the venue for the pinnacle of the jump season. The Cheltenham Festival, takes place annually in March. Located in the county of Gloucestershire in the South West of England, the racecourse is just under ten miles away from the gently rolling hills of the Cotswolds, with its honey stone houses and market towns and the largest area of natural beauty in England.

Cheltenham Festival hosts 28 races with a prize fund of over £4.5 million up for grabs according to British Racecourse’s guide. That’s why it’s no surprise the Cheltenham Festival coincides with the most significant betting week of the year, with an estimated £500 million wagered by punters. The 265,000 pints of Guinness consumed during the festival could cloud the judgment of many a punter. Still, some will be drinking the finest of Irish exports in celebration of a fantastic betting coup.

Screenshot 2020 08 05 at 15.34.16 300x225 - The Biggest Gambles That Paid Off At Cheltenham Racecourse

Son Of Flicka At The Coral Cup 2012

Very few punters would have given Son of Flicka a chance in the Coral Cup at the festival in 2012. Opening up at 66/1 on the morning of the race, the horse started to attract the money of those in the know. The bookies reacted by shortening the odds, finally going off at 16/1. With Jason Macguire on board, the Donald McCain trained horse led before the last and won by three and a half lengths. It was a gamble that saw connections to the stable walk away with vast sums of money, with owner Phil Willams alone hitting the bookies for a cool £900,000.

Coral Cup Hurting The Bookies Again

The Coral Cup was another nightmare for the bookies in 2003 when Xenophon ran away the winner under the jockeyship of Mick Fitzgerald, who kept a cool head while trying to navigate his way through a crowd of twenty-six other horses. The 20/1 on offer ante-post was soon gobbled up and opened up at 8/1 on the morning of the race. The money continued to pour in, and the horse went off the 4/1 favorite. The horse led after the last fence, pulling clear and winning with ease for trainer A.J Martin.

Mr. Donavan After A Losing Streak

Very few would have considered a punt on Mr. Donavan at the 1982 Sun Alliances Novice Hurdle having lost in his previous four hurdle races. Very few people outside of Ireland even knew of the horse, a low profile that was to pay off in style. The horse was expertly guided home by jockey Tommy Ryan, and the Edward O’ Grady trained horse duly landed the gamble after being backed from 6/1 to 9/2, a lot shorter than the 14/1 the owner was expecting to get before word got out.

An Insulted Trainer Backs His Horse

The highlight of the festival, The Gold Cup, saw a considerable gamble pay off in 2000. Trainer Noel Chance thought the 50/1 on offer for his horse Looks Like Trouble, somewhat of an insult. Taking advantage of the bookmakers’ generosity, Chance helped himself and was rewarded on the day of the race as jockey Richard Johson took up the reins and led the horse home winning by five lengths at odds of 9/2. A nice little touch that Chance claimed paid for a new conservatory.

Destriero – The One The Bookmakers Will Always Remember

It may have been nearly twenty years ago, but mention the name of Destriero in the presence of some bookmakers, and you’ll still see the look of pain etched on their faces. The 1991 Supreme Novices Hurdle saw what must be one of the biggest gambles of the modern era. The horse, owned by Betty Furlong, was subject of a massive gamble involving husband Noel Furlong. Before the race, Noel settled a £500,000 VAT bill with the inland revenue, a sum he was soon to recoup.

Furlong had £300,000 on the horse at differing odds, down to 6/1. Trained by Andrew Geraghty and ridden by Pat McWilliams, the horse went off at 6/1. Although the horse hit the last fence, the betting coup was in the bag with the horse winning by four lengths, netting the owner’s husband Noel Furlong, a reported £2 million.

Although bookmakers generally come out on top in the battle of wits against the punters, it’s on those rare occasions when they are caught by surprise and stung for millions that bring a smile to the lovers of this great sport. Cunning, well planned, secretive, call it what you like, but when it happens, it’s a sight to behold, and even more so when a great sting takes place at such a prestigious racecourse as Cheltenham at the biggest jump festival of the year.


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