Which jockey has ridden the most winners at a single Cheltenham Festival?

Unsurprisingly, the jockey who has ridden the most winners at a single Cheltenham Festival is Rupert ‘Ruby’ Walsh. Walsh is, far and way, the most successful jockey in the history of the Cheltenham Festival, with 59 winners – 16 more than his nearest rival, Barry Geraghty – to his name. He retired from race riding in May, 2019, but is immortalised by the ‘Ruby Walsh Trophy’, which is presented to the leading jockey at the Cheltenham Festival each year.

Walsh, himself, was leading jockey at the Cheltenham Festival on no fewer than eleven occasions between 2004 and 2017, including five years running between 2013 and 2017. In 2009 – the year in which he won the Queen Mother Champion Chase on Master Minded, the World Hurdle on Big Buck’s and the Cheltenham Gold Cup on Kauto Star, all trained by Paul Nicholls – Walsh rode seven winners in total, setting a new record. Seven years later, in 2016, he equalled his own record by again riding seven winners, all trained by Willie Mullins, including Annie Power in the Champion Hurdle. In 2021, Rachael Blackmore, who rode six winners to become the first female jockey to win the Ruby Walsh Trophy, came as close as anyone else ever has to equalling the record.