Saffie Osborne made history as she became the first woman to ride the winner of a British classic as Highwayman led home a Joseph O’Brien one-two in the Betfred St Leger at Doncaster on Saturday.
SAFFIE OSBORNE – THE FIRST FEMALE JOCKEY TO WIN A BRITISH CLASSIC!
— At The Races (@AtTheRaces) September 12, 2026
HIGHWAYMAN WINS THE 250TH BETFRED ST LEGER! pic.twitter.com/PgDkCG6DFG
Handed the plum spare ride on the improving Vinnie Roe Stakes winner as just reward for a fine season, the eye was drawn to the 24-year-old who was moving stylishly into contention as the runners entered the long Doncaster straight.
With the Ballydoyle contingent seemingly beaten off as Osborne sent her mount on with a furlong to run, the only danger appeared Billy Loughnane and 5/2 second-favourite Enceladus.
However, Highwayman (11/1) was not for reeling in under an inspired Osborne who entered the record books on the 250th anniversary of the world’s oldest classic.
Osborne told ITV Racing: “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.
“I didn’t have a ride in the race on Monday morning, let alone one with a chance, and I can’t thank so many people enough. Firstly Joseph and his team for putting their faith in me, it won’t change Joseph’s life, but it will change mine.
“My agent Tony Hind, I would be nowhere without him and I know it’s cliched but my mum, dad and whole family. 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.
“I was more forward than I anticipated, but he was travelling so well into it, I couldn’t believe it.”
Delighted winning owner John Neocleous said: “The horse did it so easy didn’t he. I wish I could say more about it, but I’m still in shock!
“This horse was 250/1 in a maiden (at Naas in June), that was the wrong distance of course, but it’s amazing how far he has come. We should not be surprised, though, because Joseph keeps on making history.
“You don’t know where this horse will end up, but he did win pretty easily today.
“We’re going to Australia, I think, but Joseph will make the decisions, he’s in charge.
“We won the Galway Plate a month ago with King Alexander so it’s been a hell of a summer but this is a different level completely.”
Regarding his history-making jockey he said: “Saffie is amazing, I’m sure she’s in shock as well.
“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 and history’, but I didn’t really believe it!”
O’Brien watched the race from Leopardstown where he told Racing TV: “The two of them are two really nice, progressive stayers.
“It’s a special race and he was impressive I thought.
“He was a slow learner and mentally he was immature, but when he got rolling he improved hand over fist.
“Enceladus is a huge big horse and he’ll make a smashing four-year-old.”


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