Osborne Makes History as First Woman to Win British Classic on Highwayman

Saffie Osborne etched her name into the record books on Saturday by becoming the first female jockey to win a British Classic. Riding Joseph O’Brien’s Highwayman, she claimed victory in the 250th running of the Betfred St Leger at Doncaster, marking a historic milestone for the sport.

Osborne secured the ride as a spare after originally having no mount in the feature race, a reward for a strong season. The 24-year-old guided the Vinnie Roe Stakes winner from the Ballydoyle yard into contention as the field entered the long home straight. Although Billy Loughnane’s Enceladus posed a late threat as the 5-2 second favorite, Highwayman held firm to win by an 11-length margin, with Amelia Earhart finishing third.

In her post-race interview with ITV Racing, a visibly emotional Osborne expressed her disbelief at the achievement. “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,” she said. “I didn’t have a ride in the race on Monday morning, let alone one with a chance.”

She extended her gratitude to O’Brien and his team for their trust, noting that while the win would not alter the trainer’s career, it would “change mine.” Osborne also thanked her agent, Tony Hind, and her family, adding, “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.”

She reflected on her tactical approach during the race: “I was more forward than I anticipated, but he was travelling so well into it, I couldn’t believe it.” The win arrived on the 250th anniversary of the world’s oldest Classic, capping off a significant weekend at Doncaster.