From a problematic knee injury to making history in the St Leger: charting Saffie Osborne's stratospheric rise

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Victory aboard Highwayman in the Betfred St Leger capped a remarkable season in the saddle for Saffie Osborne, who on Saturday became the first woman to ride the winner of a British Classic.

Osborne, 24, may be 17 winners away from her personal best of 87 domestic winners in 2024, but she has been an emerging force at the top table this term and victory in the St Leger on her first ride for Joseph O'Brien means her mounts have earned more than £2.3 million in prize-money in Britain since January.

A dream 2026 has followed a challenging 2025, when a serious knee injury curtailed her year, but she has been in sterling form since her return.

As well as captaining the winning team at this year's Shergar Cup, she was just a length and a half away from winning her first Group 1 when Touleen finished runner-up in the Coronation Stakes at Royal Ascot in June. She also partnered Inis Mor to win at Listed level in May and enjoyed a big pay day when Zigazig Ah won the Super Sprint in July.

Shergar Cup winners Ryan Moore, Saffie Osborne and Dylan Browne McMonagle

Saffie Osborne captained a Shergar Cup team including Ryan Moore and Dylan Browne McMonagle to victoryCredit: Getty Images

From talented eventer to the weighing room

The daughter of stylish jump jockey and Group 1-winning trainer Jamie, Osborne was a talented eventer in her youth, but chose to follow her father into the weighing room.

She rode under rules for the first time in 2020, with Hot Scoop providing her with her first winner at Windsor on her 13th ride.

Ed Walker proved as significant as any trainer in Osborne's early career and was responsible for her first Group-race victory when Random Harvest landed a Group 3 in Italy in 2022. She partnered the same mare to win the Group 3 Valiant Stakes at Ascot the following year.

Osborne and Random Harvest twice finished runner-up at Royal Ascot, beaten a neck when second in the Kensington Palace Stakes in 2022 and pipped by the same margin in the following year's Group 2 Duke of Cambridge Stakes.

Agent switch opens doors

After scoring yearly tallies of nine, 40 and 46 winners in her first three years, Osborne joining forces with agent-to-the-stars Tony Hind in 2023 helped lift her to 70 domestic winners, opening the door to ride for trainers such as Owen Burrows and Richard Spencer. She also continues to partner the majority of her father's runners in Britain and abroad.

She was the first female rider to win a race at Meydan in 2024 and 24 hours later scored in Doha. She has ridden in two legs of the US Triple Crown, partnering Heart Of Honor to finish fifth in the Preakness Stakes at Pimlico and sixth in the Belmont in 2025. She rode the same horse, who is trained by her father, to finish seventh in the Dubai World Cup in March.

She rode in a British Classic for the first time when partnering Walker's Ten Bob Tony to finish eighth to Notable Speech in the 2,000 Guineas in 2024, but Highwayman appeared to be her best shot at Classic glory to date and she did not disappoint when guiding the O'Brien-trained three-year-old to a two-and-a-half-length success at Doncaster.

Hollie Doyle was the first female jockey to be placed in a British Classic when she finished third on Nashwa in the 2022 Oaks at Epsom and she went on to win the French equivalent the same year. That made her the first woman to partner the winner of a major European Classic, but it is Osborne who goes down as the first woman to ride the winner of a British Classic, and there is the promise of more to come.

Milestones for female jockeys on the Flat

Ina Schwarzkachel is the first woman to ride a national Derby winner when partnering Cleopatra to victory in the Nederlandse (Dutch) Derby in 1971.
Gay Kelleway is the first female jockey to ride in a British Classic when last on Davemma in the 1986 Oaks.
Sibylle Vogt is the first female jockey to win a Classic that is part of the European Pattern when landing the German 1,000 Guineas (Group 2) on Novemba in 2021.
Hollie Doyle is the first female jockey to win a Group 1 European Classic when triumphing in the Prix de Diane on Nashwa in 2022.
Amateur Nina Baltromei is the first female jockey to win a national Derby that is part of the European Pattern when winning the Deutsches Derby on Hochkonig in 2025.
Saffie Osborne is the first female jockey to win a British Classic when triumphing in the 250th St Leger on Highwayman in 2026.

Compiled by John Randall

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