Saffie Osborne made history in the Doncaster St Leger aboard Highwayman
The 24-year-old jockey became the first woman to win a British Classic by guiding the Joseph O’Brien trainee to victory, completing a 1-2 finish with Enceladus. The historic feat arrived in the 250th running of the world's oldest Classic
DONCASTER, England (Special for Turf Diario).— The St Leger (G1-2912m, turf) celebrated its 250th anniversary by writing one of the most significant chapters in its entire history. Saffie Osborne guided Highwayman to victory this Saturday at Doncaster, becoming the first female jockey to win one of the five British Classics and adding an even greater dimension to an edition that was already historic before the gates opened.
Osborne, just 24 years old, did not even have a confirmed ride in the race at the start of the week. She ended up receiving the call aboard the ascending Joseph O’Brien trainee and capitalized on the opportunity in a manner she will hardly ever forget.
Previously winner of the Vinnie Roe Stakes (L), Highwayman arrived on a clear upward trajectory, though remaining far from the center of attention among the favorites. However, early on it became evident he had plenty to offer.
Osborne positioned him closer to the pace than originally planned, but without fighting him. Highwayman traveled comfortably, and as the field turned into Doncaster's long home straight, he began to make his move while the main Ballydoyle contenders started to falter.
The jockey bided her time until finding the right moment and, with 200 meters left to run, set Highwayman loose toward the lead.
At that juncture, second-choice Enceladus (Sea the Stars), ridden by Billy Loughnane and also conditioned by Joseph O’Brien, made his run. He proved to be the only rival capable of seriously threatening the leader, but Highwayman dug deep to hold his ground, allowing Osborne to seal a flawless ride.
Crossing the wire unleashed a celebration that reached far beyond the sporting outcome. After two and a half centuries of the St Leger and all the accumulated tradition of the British Classics, a female jockey had won one for the very first time.
“I don’t think I’ve ever been speechless in my life,” Osborne confessed to ITV Racing while still trying to process the achievement. “On Monday morning I didn’t even have a ride in the race, let alone one with a chance. I can’t thank so many people enough.”
The rider expressed special gratitude for the confidence shown by Joseph O’Brien and his team, alongside the work of her agent Tony Hind and the unwavering support of her family.
“This isn’t going to change Joseph’s life, but it’s going to change mine,” she summarized, before admitting she hit the wire in complete shock.
For Joseph O’Brien, the afternoon proved equally extraordinary. Not only did he capture the final Classic of the British season, but he also swept the top two spots with Highwayman and Enceladus, confirming the outstanding form of his stable.
Yet no statistical milestone could compete this time with the name of Saffie Osborne.
The St Leger was inaugurated in 1776 and reached its 250th running established as the oldest Classic in world racing. Some of the greatest thoroughbreds and jockeys across eras have graced its history.
In 2026, it finally unlocked a door that had remained shut. Highwayman won the St Leger, Joseph O’Briencompleted the 1-2 finish, and Saffie Osborne stamped her name permanently into the history of British racing.
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