Highwayman won the 2026 St Leger at Doncaster on September 12, giving jockey Saffie Osborne a landmark victory in the 250th running of Britain’s oldest Classic.
The Joseph O’Brien trained Highwayman defeated stablemate Enceladus, with Amelia Earhart finishing third. The result delivered a major one two finish for the O’Brien stable and transformed one of the most historic editions of the race into a milestone for British racing.
Osborne becomes the first woman to win a British Classic
Osborne became the first female jockey to win one of the five British Classics. She entered the race on a late opportunity aboard Highwayman and produced the defining result of her career at Doncaster.
Highwayman arrived as a progressive stayer after winning the Vinnie Roe Stakes at Leopardstown. He had already shown that the extended distance suited him, and he carried that progression into the Group 1 test.
Joseph O’Brien takes the first two places
Enceladus came into the St Leger as one of the leading contenders after an unbeaten 2026 campaign that included the Gordon Stakes. He finished second behind his stablemate, giving Joseph O’Brien the top two places in the Classic.
Amelia Earhart completed the first three, while Derby winner Christmas Day was unable to produce the result expected from one of the most prominent runners in the final field.
A historic St Leger in the race’s 250th year
The St Leger was already carrying unusual significance in 2026 because the Doncaster festival was celebrating 250 years of the Classic. Highwayman’s victory added another permanent chapter to the race’s history.
For more background, read the OTB Bet St Leger Stakes guide, the final St Leger preview and the St Leger Festival guide.
Featured image: Peter Glyn via Wikimedia Commons. Licensed under Creative Commons Attribution Share Alike 4.0.
