Saffie Osborne has become the first female jockey to win one of British Flat racing’s five Classics, riding Highwayman to victory in the St Leger at Doncaster.

The 24-year-old burst clear of the field on the 11-1 chance in the closing stages to create history in the 250th anniversary of the world’s oldest Classic Flat race.

It was a one-two for winning trainer Joseph O’Brien, whose colt Enceladus (5-2) finished second, two-and-a-half lengths back.

Aidan O’Brien was bidding to become just the third trainer to win a fourth consecutive St Leger but had to be content with third with Amelia Earhart (22-1).

Pre-race favourite Christmas Day (7-4) was heavily backed to give Aidan O’Brien that historic fourth victory in a row and complete the Derby-St Leger double, but finished well down in ninth place.

“I definitely didn’t have this on the bingo card this week,” Osborne told ITV Sport immediately after the historic victory in the fifth and final Classic of the British Flat season.

“I didn’t even know if I would be riding the St Leger on Monday morning.”

No female jockey has won any of the other four Classics – the 1,000 Guineas and 2,000 Guineas at Newmarket and the Oaks and Derby at Epsom.

Osborne was quick to thank the trainer for giving her the ride, adding: “I have to thank Joseph and his team for putting their faith in me. It won’t change Joseph’s life, but it’s changed mine.”

The jockey is the daughter of trainer and former top National Hunt jockey Jamie Osborne, while her mother, Katie O’Sullivan, is a highly-regarded equine artist.

She started as an apprentice in 2020 and finished second in the apprentice championship the following season.

Osborne went on to be crowned leading jockey in the Racing League for three consecutive seasons from 2022 to 2024.

In 2024, she became the first female jockey to win a race at the Dubai Carnival, on Ouzo, while her first Classic ride came in the same season, finishing eighth on Ed Walker’s Ten Bob Tony in the 2,000 Guineas.

Like Rachel Blackmore, the first female jockey to win the Grand National, her name will now go down in racing folklore.

Joseph O’Brien was at Leopardstown for the Irish Champion Stakes on Saturday, but delighted Highwayman owner John Neocleous was at Doncaster to share the moment with Osborne.

“Saffie is amazing, I’m sure she’s in shock as well,” he said after watching her storm clear at the end of the one mile six furlong trip.

“Joseph came up with the idea, but he called me first and I was extremely happy to have her. She’s an up-and-coming jockey, she knows how to ride a finish and I thought if she rode a good finish maybe we’d be placed.

“But she won comprehensively so I’m very happy. I said to Saffie, ‘let’s go and make history’, but I didn’t really believe it!”

The surprise victory continues trainer Joseph O’Brien’s love affair with the St Leger.

He won the race as a jockey on Leading Light in 2013 and claimed his first victory as a trainer in 2020 with Galileo Chrome.

Enceladus was expected to be his best chance to double his number of winners in the famous old race, having hit top form this season with three big victories, including in the Gordon Stakes at Goodwood.

But Highwayman had also showed rapid improvement this year, especially in winning the Vinnie Roe Stakes at Leopardstown.