‘I still can’t believe it, I’m in shock’ – Saffie Osborne lands historic Leger victory

‘I still can’t believe it, I’m in shock’ – Saffie Osborne lands historic Leger victory

By Racing TV
Last Updated: Sat 12 Sep 2026
When a race has been going for 250 years like the Betfred St Leger, it would be reasonable to think all bases have been covered in terms of stories. But enter Saffie Osborne to make history as the first woman to ride the winner of a British Classic.
Hollie Doyle, in whose footsteps Osborne is quite clearly following, does have a French Classic on her CV, but while she recuperates from a serious leg injury she has been beaten to the punch by Osborne, who delighted the huge 30,000-plus crowd at Doncaster.
Trained by Joseph O’Brien, who also saddled second home Enceladus, Osborne’s mount Highwayman was incredibly sent off at 250-1 for a Naas maiden in June. Since then he had won at Killarney, taken a Listed race at Leopardstown and now the world’s oldest Classic, for which he returned at 11-1.
Osborne, who is the daughter of former National Hunt jockey and now trainer Jamie, said: “I’m in shock! I burst into tears!
“I was in front and I knew I hadn’t seen anyone from two out and then I felt Billy (Loughnane, on Enceladus) come to my girth, but he went again and going across the line… I’ve never celebrated before as I’ve never won a race good enough to celebrate, but to win that was incredible.
“It was really weird, this morning I just had a really good feeling about today. You are always quite hesitant to say that, as most of the time you are wrong. I’m just in shock, I didn’t have that on my bingo card for the week, I didn’t have a ride in the Leger this time last week.
“I found out on Tuesday, it just appeared on my booked rides and I thought, ‘oh I’ve got a ride in the Leger – oh jeez, I’ve got quite a good ride in the Leger!’.”
Presented with her prize by the Princess Royal, Osborne was already the first woman to win a race in the UAE and from just her third attempt, she is now a Classic winner.
“I was more forward than I’d planned to be, but he travelled so beautifully I didn’t mind hitting the front sooner than planned if I was going to hit the front. But he kept going well and he’s obviously trained by an absolute master in Joseph,” she said.
Saffie Osborne celebrates as she crosses the line on Highwayman (Richard Sellers/PA)
“It was just a real honour to even pick up the ride, never mind win a Classic. It’s something we all want to do, but did I think at the start of the year I was going to win a Classic? Absolutely not. I think I’m going to start crying again now.
“When I saw it was the 250th year I thought, ‘surely there has to be a good story this year’, and I just thought a girl winning it was quite a nice one after 250 years!
“This is the kind of thing that changes your life, no one can take it away from you, I still can’t believe it, I’m in shock.
“Hayley (Turner) and Hollie are two people I’ve looked up to enormously, they all had their firsts of doing things and this is mine.”
Highwayman holds an entry in the Melbourne Cup and Osborne confessed to already thinking that far ahead in November.
She said: “I’m not going to lie, knowing he was in the Melbourne Cup I thought if he finished third he’d have a light weight and I’d be able to ride him. I think he’ll have a bit more now though! Dylan (Browne McMonagle) will be back by then and I don’t care, for what this horse has done for my career I’ll love him forever!
“My dad sent me a message saying, ‘soft hands, good luck’, so not a huge amount, but he’s never been one to give me loads of advice.
“I have to say thank you to my agent (Tony Hind), to Joseph O’Brien, my team, but the biggest thank you is to my parents and grandparents who have never missed a race of mine between them. I know the first message on my phone will be my granny and she’ll probably be the first I respond to.”
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, 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.
Saffie Osborne is presented with the trophy by the Princess Royal (Richard Sellers/PA)
“We’re going to Australia, I think, but Joseph will make the decisions, he’s in charge.”
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!”
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