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.

The Cheltenham Gold Cup was first run, as a steeplechase, in 1924 but, surprisingly, the winner of what is, nowadays, the most prestigious race in the British National Hunt calendar has been disqualified just once. The unfortunate horse in question was Tied Cottage, trained by Dan Moore and ridden by Tommy Carberry, who made all the running to beat Master Smudge by eight lengths in the 1980 renewal of the Cheltenham Gold Cup. However, a post-race urine test revealed a minute trace of theobromine, a prohibited substance that has physiological effects similar to caffeine, believed to have come from a batch of contaminated foodstuff, and Tied Cottage was disqualified in favour of the runner-up at a subsequent enquiry. The disqualification was a ‘double whammy’ for connections, who had seen Tied Cottage fall at the final fence the previous year, handing the Cheltenham Gold Cup to Alverton.