Yes. In fact, three different women have trained four different horses to win the Cheltenham Gold Cup six times between them. Jenny Pitman, who made history by becoming the first woman to train the winner of the Grand National in 1983, did so again in 1984, by becoming the first woman to train the winner of the ‘Blue Riband’ event, with Burrough Hill Lad. Indeed, Burrough Hill Lad may have won the Cheltenham Gold Cup again, but for recurring leg trouble, which caused his late withdrawal from the race in 1985 and again in 1986. In any event, ‘Mrs. P.’ won the Cheltenham Gold Cup for a second time, with Garrison Savannah, ridden by her son, Mark, in 1991.
Just over a decade or so later, Henrietta Knight wrote her name into the history books by training Best Mate to win the Cheltenham Gold Cup three years running in 2002, 2003 and 2004, making him the first horse since the legendary Arkle, in the Sixties, to do so. She, too, was denied the opportunity for further success when Best Mate suffered a burst blood vessel just a week before the 2005 renewal of the race.
Last, but by no means least, of the headline-making female trainers comes Jessica Harrington who, in 2017 – at the age of 70 and having held a training licence since 1989 – won the Cheltenham Gold Cup with her very first runner in the race, Sizing John. In a strange case of history repeating itself, Sizing John was a late withdrawal from the 2018 race after suffering a fractured pelvis and remains sidelined for the foreseeable future.