Saffie Osborne makes racing history as first woman to win a British Classic

Saffie Osborne may only be 24, but like Rachael Blackmore before her, she is on course to leave a lasting impression in a male-dominated industry.

Just as Blackmore smashed a glass ceiling in becoming the first woman to ride the winner of the Grand National, Osborne is the first partner the winner of the St Leger, the world’s oldest Classic, in its 250th year. For that matter, she is the first to win any British Classic after triumphing with Highwayman.

Osborne told ITV Racing: “I don’t think I’ve ever been speechless in my life and I didn’t have this on the bingo card for this week. I didn’t have a ride in the race on Monday morning, let alone one with a chance, and I can’t thank so many people enough. Firstly Joseph and his team for putting their faith in me, it won’t change Joseph’s life, but it will change mine.

“This means the absolute world and as I crossed the line I was in shock. I just can’t believe it and it just doesn’t feel real. I was more forward than I anticipated, but he was travelling so well into it, I couldn’t believe it.”

Daughter of trainer and former top National Hunt jockey Jamie, her mother Katie O’Sullivan is a highly regarded equine artist so she is certainly bred for the job, and had a successful spell eventing before turning to racing.

Keen to expand her horizons after leaving school, Osborne spent time with Aidan O’Brien in Ireland before going further afield to learn from Australian trainer Gai Waterhouse. She had her first season as an apprentice in 2020, with her first winner coming in July, although that was cut short when a bad fall at Windsor saw her suffer concussion, broken ribs, a broken arm and a punctured lung.

Highwayman ridden by Saffie Osborne on their way to winning the St Leger Stakes at Doncaster. Photograph: Richard Sellers/PA

Something so serious could have seen a promising career end before it had really started, but she came back stronger the following season to finish second in the apprentice championship to Marco Ghiani. It was in the Racing League where she really came to the attention of the wider world, though, being crowned leading jockey for three successive years between 2022-2024.

A first Group-race win came on Ed Walker’s Random Harvest in 2022 in Italy and the following year the same horse provided her with a British Group race in the Group Two Valiant Stakes. She won the Chester Cup on Harry Fry’s Metier in 2023 and to prove she liked the team environment also won the Shergar Cup as part of the Girls team.

Other notable firsts include being the first female to win a race at the Dubai Carnival on Ouzo, trained by her father, in February 2024. The following day she won a valuable sprint in Qatar on Emaraaty Ana, also trained by her dad.

Her first Classic ride came on Walker’s Ten Bob Tony in the 2000 Guineas two years ago, finishing eighth, while in 2025 back in Dubai she struck up a great partnership with Heart Of Honor, whom she would go on to ride in the Preakness and Belmont Stakes, two legs of the American Triple Crown.

This season Osborne has kicked on again, and then some. Not only has she captained Ryan Moore and Dylan Browne McMonagle to victory in the Shergar Cup, she rode a treble at Ascot on King George day and a Glorious Goodwood double.

And now has her own place in the history books.