The short answer is three, although those three female trainers are actually responsible for six Cheltenham Gold Cup victories between them. Jenny Pitman, who had already made history by becoming the first woman to saddle a Grand National winner in 1983, wasted no time when repeating the dose in the Cheltenham Gold Cup in 1984, courtesy of Burrough Hill Lad. She also won the ‘Blue Riband’ event again in 1991, with Garrison Savannah, ridden by her son, Mark.
Just over a decade later, in the wake of an outbreak of foot-and-mouth disease, which caused the 2001 Cheltenham Festival to be abandoned, Henrietta Knight saddled Best Mate to a notable hat-trick in the Cheltenham Gold Cup in 2002, 2003 and 2004. He became the first horse since the legendary Arkle, 38 years earlier, to win the race three years running.
Last, but by no means least, Irish trainer Jessica Harrington saddled Sizing John to win the Cheltenham Gold Cup in 2017. Mrs. Harrington, 70, was having her first runner in the race and later joked about ‘beginner’s luck’, despite having previously won the Queen Mother Champion Chase (twice) and the Champion Hurdle.
After he had given 17lb and upwards away to his rivals when recording a game, albeit narrow, victory, on heavy going, in the Castleford Handicap Chase at Wetherby in December, 2020, Kim Bailey described First Flow, who was completing a five-timer, as an ‘extraordinary horse’. However, the Andoversford trainer had further cause for celebration the following month, when the 9-year-old belied odds of 14/1 to win the Grade One Clarence House Chase at Ascot and, in so doing, beat the reigning two-mile champion chaser, Politologue, by 7 lengths at level weights.
Victory in the Clarence House Chase was also notable for the fact that it was the first time in 9,443 days, or 25 years, 10 months and 5 days, that Bailey had saddled a Grade One winner. Remarkably, his last winner at the highest level was Master Oats, ridden by the long-retired Norman Williamson, in the Cheltenham Gold Cup in 1995! To be fair, having won the Champion Hurdle 48 hours earlier with Alderbrook, Bailey was completing the Champion Hurdle – Cheltenham Gold Cup double, making him the last trainer to do so. Nevertheless, fans of nostalgia might like to know that, at the time, John Major was Prime Minister, a pint of lager cost £1.66 and ‘rogue trader’ Nick Leeson had just caused the collapse of Barings Bank.
However, the first female jockey to ride a winner at the Cheltenham Festival was Caroline Robinson (née Beasley), who won the Foxhunter Chase – a race restricted to amateur jockeys – on her own horse, Eliogarty, in 1983. Originally bought by her father, Jeremy, and trained in Co. Claire, Ireland, by John Hassett, Eliogarty was once described by Robinson as ‘the greatest present anyone’s ever given me’. Three years later, Robinson won the Aintree Foxhunters on the same horse, therbey becoming the first female jockey to ride a winner over the Grand National fences, too.
Back at the Cheltenham Festival, though, the first female jockey to ride a winner against fully fledged professionals was Gee Armytage who, in 1987, won the Kim Muir Challenge Cup on The Ellier, trained by Nigel Tinkler. Just for good measure, at the same Festival, Armytage also won the Mildmay of Flete Challenge Cup on the aptly-named Gee-A, trained by Geoff Hubbard. She came close to making further history by winning the leading jockey award – the first female jockey to actually do so was Rachael Blackmore in 2021 – but lost out on ‘countback’ to Peter Scudamore.
Rachael Blackmore took most of the headlines at the 2021 Cheltenham Festival, becoming the first woman to win the Champion Hurdle, on Honeysuckle, and the first woman to win the Ruby Walsh Trophy, presented to the leading jockey at the meeting. However, in the ‘Blue Riband’ event itself, the Cheltenham Gold Cup, Blackmore and her mount, A Plus Tard, were usurped by lesser-fancied stablemate Minella Indo, ridden by Jack Kennedy, who stayed on gamely to win by 1¼ lengths.
In fairness, Minella Indo had looked a desperately unlucky loser in the 2020 RSA Insurance Novices’ Chase at the 2020 Cheltenham Festival, where he was unable to withstand an extraordinary finishing effort from Champ, who made up fully 8½ lengths from the final fence. After two easy wins at Wexford and Navan at the start of the 2020/21 season, Minella Indo had fallen before halfway in the Savills Chase and finished only fourth of five in the Paddy Power Irish Gold Cup, both at Leopardstown, en route to the Cheltenham Festival.
However, the form of his Cheltenham Gold Cup win looks pretty solid, with previous dual winner Al Boum Photo only third, beaten 5½ lengths, and a yawning 24-length gap back to the 2018 winner, Native River, in fourth place. Minella Indo has done all his winning on good to soft, or softer, going, so unseasonably warm weather would not be in his favour. That would appear to be his only negative and, while he has the feted novice Monkfish to contend with this time around, he fully deserves his position at the head of the ante-post market.