24-year-old star captures the 250th St Leger aboard Highwayman at Doncaster, writing a new chapter in British racing history

DONCASTER, England — September 12, 2026 — British racing witnessed a landmark moment on Saturday as Saffie Osborne became the first female jockey in history to win a British Classic, guiding Highwayman to victory in the 250th running of the Group 1 St Leger Stakes at Doncaster Racecourse.

At only 24 years old, Osborne accomplished something no woman had previously achieved across the five races that define Britain’s Classic tradition: the 2,000 Guineas, 1,000 Guineas, Epsom Derby, Epsom Oaks and St Leger.

And she did it in the oldest of them all.

Riding the rapidly improving Highwayman for trainer Joseph O’Brien, Osborne defeated stablemate Enceladus, completing a one-two finish for O’Brien, while Amelia Earhart finished third.

For a race first staged in 1776, Saturday’s 250th edition will now forever carry Osborne’s name in its history.

A Classic victory few could have predicted

The opportunity itself came somewhat unexpectedly.

Highwayman was not originally considered among the most obvious Classic contenders. The son of Persian King had been well beaten in his first four starts, but his career changed dramatically when Joseph O’Brien stretched him out in distance.

He broke his maiden at Killarney by nine lengths before stepping up to Listed company and winning the Vinnie Roe Stakes at Leopardstown over 1 mile and 6 furlongs, essentially the same stamina test he would face at Doncaster.

Osborne only learned earlier this week that her agent, Tony Hind, had secured the ride.

She admitted before the race that when Hind told her he had found her a St Leger mount, she initially imagined it might be a huge outsider. Instead, she discovered she would partner a progressive colt arriving off consecutive victories and already proven over the Classic distance.

It turned into the opportunity of a lifetime.

Highwayman delivered when it mattered most — and Osborne delivered with him.

The result also gave trainer Joseph O’Brien a remarkable one-two in Britain’s final Classic of the season, with Highwayman defeating Enceladus.

The significance of the moment

Women have been steadily rewriting the record books in European racing, but victory in a British Classic remained one of the sport’s most significant remaining barriers.

Hollie Doyle came closest when she became the first female jockey to finish in the placings of a British Classic, taking third aboard Nashwa in the 2022 Epsom Oaks. Weeks later, Doyle and Nashwa won the Prix de Diane in France, making Doyle the first female rider to capture a major European Classic.

But no woman had won one of Britain’s five Classics.

Until Saffie Osborne.

That she achieved the milestone in the 250th St Leger adds another dimension to the accomplishment. Founded in 1776 and named after Colonel Anthony St Leger, the race is recognized as the world’s oldest Classic and serves as the final leg of Britain’s traditional Triple Crown.

Two and a half centuries of history — and Osborne has now written an entirely new page.

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Who is Saffie Osborne? From eventing prodigy to Classic-winning jockey

Born March 11, 2002, Saffron “Saffie” Osborne grew up surrounded by horses and racing.

She is the daughter of Jamie Osborne, the former National Hunt jockey who became a successful Flat trainer, and equine artist Katie O’Sullivan. But despite that racing pedigree, Saffie’s first major competitive success actually came outside racing.

She was an accomplished event rider, winning six medals at pony, junior and youth European championships before eventually deciding to pursue a career as a professional jockey.

Her education was international from the beginning. Before launching her British riding career, Osborne spent time riding work for Aidan O’Brien in Ireland and legendary Australian trainer Gai Waterhouse, gaining experience in two of the world’s most demanding racing environments.

She became an apprentice jockey in 2020.

Her first winner came that summer aboard Hot Scoop at Windsor, trained by her father. Remarkably, it came on only her 13th ride. She finished her first season with nine victories before exploding onto the scene with 40 winners in 2021, finishing runner-up in the British apprentice jockeys’ championship.

Her rise, however, was not without adversity.

Only months after beginning her career, Osborne suffered a frightening fall at Windsor in October 2020 that left her with broken ribs, a punctured lung, concussion and a broken arm. She recovered and returned to establish herself as one of Britain’s most promising young riders.

From promising apprentice to international winner

By 2022, Osborne’s career was accelerating.

She became the Racing League’s leading jockey and recorded her first Group victory aboard Random Harvest in the Group 3 Premio Elena e Sergio Cumani at San Siro in Italy.

Then came 2023.

Osborne enjoyed one of her biggest early victories when partnering Metier to win the Chester Cup, followed by her first British Group success when Random Harvest captured the Group 3 Valiant Stakes at Ascot.

She finished that season with 70 winners, firmly establishing herself beyond the apprentice ranks.

Making history around the world

Osborne’s growing reputation quickly extended beyond Britain.

In February 2024, she partnered Ouzo to victory at Meydan, becoming the first female jockey ever to ride a winner at Dubai’s famous racecourse.

Less than 24 hours later, she traveled to Qatar and won again, capturing the Dukhan Sprint in Doha.

That same year she received her first opportunity in a British Classic, riding Ten Bob Tony in the 2,000 Guineas at Newmarket.

Her international profile continued growing in 2025 when Heart Of Honor took her to the United States for two legs of the American Triple Crown. Osborne finished fifth in the Preakness Stakes and sixth in the Belmont Stakes, adding another major racing jurisdiction to an increasingly international résumé.

A spectacular 2026 season

Everything appeared to be building toward 2026.

Osborne entered Saturday’s St Leger in arguably the finest form of her career.

Among her highlights this season were a treble at Ascot on King George day, a double at Glorious Goodwood, and victory aboard Zigazig Ah in the valuable Weatherbys Super Sprint.

She also captained Great Britain & Ireland to victory in the Shergar Cup, leading a team that included some of Europe’s leading riders.

And Osborne was already knocking on the door of a first Group 1.

She partnered Touleen in both the 1,000 Guineas and Coronation Stakes, finishing second to Precise in the latter at Royal Ascot.

The breakthrough finally arrived at Doncaster.

And it wasn’t simply a Group 1.

It was a British Classic.

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A career already filled with milestones — at only 24

Osborne’s résumé is extraordinary considering her age:

• First female jockey to win a British Classic — 2026 St Leger
• 300+ career victories
• 2022 Racing League leading jockey
• Chester Cup winner aboard Metier
• First female jockey to win a race at Meydan
• Group winner in Britain and internationally
• Shergar Cup-winning captain for Great Britain & Ireland
• Preakness Stakes and Belmont Stakes appearances
• Multiple major victories at Ascot and Goodwood
• Six European eventing medals before beginning her racing career

But after September 12, 2026, one achievement will stand above everything else.

British Classic-winning jockey.

A victory bigger than one race

Saffie Osborne’s St Leger triumph represents more than another major victory for one of Europe’s fastest-rising riders.

For generations, female jockeys fought for opportunities in a sport where access to elite horses and the biggest races was extraordinarily difficult. Riders such as Hayley Turner and Hollie Doyle helped change expectations and demonstrated repeatedly that gender was no barrier to competing — and winning — at racing’s highest levels.

Now Osborne has taken the next historic step.

At 24, she has become the woman who finally broke through one of British racing’s most enduring barriers.

And perhaps appropriately, it happened in a race built around stamina.

Highwayman himself had traveled an unlikely road to Doncaster, progressing from four defeats to a maiden victory, a Listed success and now a Group 1 Classic.

His jockey’s journey has been different but equally remarkable — from European eventing medals to apprentice races, serious injury, Group victories, Dubai history, American Triple Crown appearances and ultimately the winner’s enclosure at Doncaster.

Two hundred and fifty editions of the St Leger.

Five British Classics.

And for the first time, a woman stands among their winning jockeys.

Her name is Saffie Osborne — and at only 24 years old, the newest chapter of her career may only be beginning.

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