Osborne wins at Doncaster as she guide Highwayman to victory.
Saffie Osborne may only be 24, but like Rachael Blackmore before her, she is on course to leave a lasting impression in a heavily 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 female winner of the St Leger – the world’s oldest Classic, in its 250th year.
In fact, she is the first to win any British Classic after she rode Highwayman to victory in a one-two for Joseph O’Brien at 11/1.
Handed the plum spare ride on the improving Vinnie Roe Stakes winner as just reward for a fine season, the eye was drawn to the 24-year-old who was moving stylishly into contention as the runners entered the long Doncaster straight.
With the Ballydoyle contingent seemingly beaten off as Osborne sent her mount on with a furlong to run, the only danger appeared Billy Loughnane and 5/2 second-favourite Enceladus.
However, Highwayman was not for reeling in under an inspired Osborne, who entered the record books on the 250th anniversary of the world’s oldest Classic.
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.
“My agent Tony Hind, I would be nowhere without him and I know it’s cliched but my mum, dad and whole family. 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 her attentions to racing.
Keen to expand her horizons upon 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.
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 and 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. First she captained Ryan Moore and Dylan Browne McMonagle to victory in the Shergar Cup, before she rode a treble at Ascot on King George day and a Glorious Goodwood double.
Now she has her own place in the history books.