Osborne becomes first female jockey to win a British Classic

Jockey Saffie Osborne made history on Saturday at Doncaster, riding Highwayman to victory in the St Leger, the final and fifth Classic of the British Flat racing season. It marks the first time a female jockey has won any of these prestigious races — the other four, the 1,000 Guineas and 2,000 Guineas at Newmarket and the Oaks and Derby at Epsom, remain unclaimed by women riders.

Speaking after the win, Osborne said she hadn't even been certain she would be riding on Monday morning, calling the result a complete surprise. She credited trainer Joseph O'Brien and his team for putting their trust in her, saying the victory had changed her own career even if it wouldn't change his life.

Osborne is the daughter of trainer and former leading National Hunt jockey Jamie Osborne, while her mother, Katie O'Sullivan, is a well-regarded equine artist. She began her career as an apprentice in 2020 and finished runner-up in the apprentice championship the following season. Between 2022 and 2024 she was crowned leading jockey in the Racing League for three consecutive seasons. In 2024 she became the first female jockey to win at the Dubai Carnival, and that same season recorded her first Classic ride, finishing eighth in the 2,000 Guineas.

Highwayman's owner, John Neocleous, who watched the race at Doncaster, said he had only hoped for a placing but was delighted by the decisive win. Trainer Joseph O'Brien, who was at Leopardstown in Ireland at the time, had proposed the pairing himself and offered Osborne the ride. O'Brien has a long history with the St Leger, having won it as a jockey in 2013 and claimed his first victory as a trainer in 2020.