Saffie Osborne made history on Saturday by becoming the first female jockey to win a British Classic race, guiding Highwayman to victory in the Betfred St Leger at Doncaster. The 24-year-old was a late addition to the race after the original rider, Dylan Browne McMonagle, was sidelined due to a fall at Bellewstown earlier in the week.

Riding for trainer Joseph O’Brien, Osborne took command of the 11-1 outsider with a decisive move inside the final furlong. Highwayman held off a strong challenge from stablemate Enceladus, ridden by leading apprentice Billy Loughnane, who went off as the 5-2 favourite. Amelia Earhart, trained by Joseph O’Brien’s father Aidan, finished third at 22-1 odds. The victory earned £397,000 for the O’Brien stable.

Osborne acknowledged the significance of the achievement, expressing disbelief at the rapid turn of events that saw her go from having no mount to winning the 250th running of the world’s oldest Classic. “I didn’t have a ride in the race on Monday morning, let alone one with a chance,” she said. Osborne also thanked Joseph O’Brien and his team for their confidence, as well as her family and agent, Tony Hind, for their support.

This milestone adds to the recent progress of female jockeys in Classic races. Last year, Hollie Doyle became the first woman to place in a British Classic, finishing in the Oaks, and also claimed her first European Classic victory aboard Nashwa in France’s Prix de Diane.

In related racing news, Darkness Falls emerged as the 7-1 favourite for next year’s English Derby after a commanding performance in the HKJC World Pool Golden Fleece Stakes at Leopardstown. Under Ryan Moore, the Aidan O’Brien-trained colt secured a Group One victory over an extended distance, demonstrating strong finishing speed in a fiercely contested race. Trainer Aidan O’Brien praised the effort, describing Darkness Falls as “very exciting” and noting the demanding nature of the race, which was run as a Group One for the first time. The victory adds Darkness Falls to a distinguished list of Ballydoyle-trained horses who have gone on to Derby success, following in the footsteps of Diego Velazquez (2023) and Benvenuto Cellini (2025).