Fitzdares, Racing Bookmaker of the Year, consider the greatest races and horses in Cheltenham's history

Fitzdares consider the greatest win in Cheltenham Gold Cup history ahead of this year’s race.

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The first recorded race winner at Cheltenham, when the track was at Cleeve Hill, was a mare, Miss Tidmarsh, in 1818. The Festival was born in 1860, events taking their current format at Prestbury Park in 1911.


The Blue Riband of the National Hunt season was established in 1924. Horses run three miles 2½ furlongs, left-handed, over 22 fences. Open to any horse aged five years or older, only three have won it at that age, including 5/1 Red Splash in 1924. The oldest horses to win the race: Silver Fame in 1951 and What A Myth in 1969, both 12.

The Gold Cup is the third race of the Stayers Chase Triple Crown, a £1m bonus paid to any horse that wins the Betfair Chase, the King George VI and the Cheltenham Gold Cup in the same season. Kauto Star is the only horse to have achieved this feat since it was introduced in 2005.

This year, nine-year-old Al Boum Photo, in Mrs J Donnelly’s colours, will bid for his Gold Cup hat-trick, an achievement only matched by four horses: Golden Miller (pictured), Cottage Rake, Arkle and Best Mate. Golden Miller won five times between 1932-36, while Arkle’s wins from 1964-66 earned him the highest-ever Timeform steeplechase rating at 212 and a race at the Festival named in his honour: The Arkle Challenge Trophy. Meanwhile, Best Mate (2002-04), never fell over a fence or hurdle in his 22-race career. His jockey, Jim Culloty, is the uncle of flat-racing superstar and champion jockey Oisin Murphy.

Willie Mullins is the most successful trainer in Cheltenham history, with 72 wins, ahead of current rivals Nicky Henderson and Paul Nicholls, but only totted up his first Gold Cup victory with Al Boum Photo in 2019. But can anything surpass what Michael Dickinson managed in 1983? He trained home the first five in the race with Bregawn, Captain John, Wayward Lad, Silver Buck, and Ashley House, in that order. That said, Norton’s Coin somehow getting his nose ahead of Desert Orchid at staggering odds of 100/1 in 1990 is a worthy claim for most spectacular race result in history.

For the bookmaker and punter alike, Cheltenham is a never-ending cautionary tale. We’ve had at least six months to eye up this season’s challengers, and years more in most cases. Our prices are chalked up on the back of chunks of data and the keen eyes of our horse-racing team. In other words, rock solid. At least, that’s what we think. Just don’t mention the terrible accumulator that culminated in Nicanor beating Denman in 2006. Or when Denman won the Gold Cup. Or… actually, anything Denman related. But it ebbs and, well, gushes.

In 2015, Annie Power was the fourth horse to run for Willie Mullins and jockey Ruby Walsh on the first day of the Festival. The first three, Douvan, Un De Sceaux and Faugheen had romped home. Her dramatic last-hurdle fall spared the industry a staggering £50 million and almost certainly kept Fitzdares’ head above water.

And the apocryphal story about Lucian Freud losing a million to one bookmaker and offering to repay his debt with a painting? We’d probably insist on a cheque unless he could paint a better picture for 2021. Either way, win or lose, as long as Cheltenham is on, racing fans are happy.


Delta Work: not much has gone right for him this season but you can strike a line through his past two runs — he is always a better horse in the spring. He was only beaten six lengths in this race last year, when everything that could go wrong did. Still only an eight-year-old, this five-time Grade 1 winner is the forgotten horse in the Gold Cup.

By Fitzdares