“I said at the start of this year that if I rode 14 winners this season, I would be delighted,” says 23-year-old National Hunt jockey Lilly Pinchin. The talented rider from Gloucestershire now has 21 winners in the bag, and counting – the jumps’ season runs to the end of April, so there’s plenty of scope for her to add to this tally.
Lilly has ridden some big winners this season, on her way to beating her previous personal best of 14. But her roots aren’t steeped in racing or equestrianism.
“My family weren’t into racing at all – my mum was brought up in Coventry – but my aunty had a horse she hacked out a bit,” explains Lilly. “I was lucky to have ponies from a young age that taught me how to ride and was a member of the North Cotswold Hunt branch of the Pony Club.”
Lilly embraced a wide range of activities with her ponies, with success in a variety of disciplines.
“When I was nine, I got a pony called Magical Toffee; a 12.2hh, long-legged, fine built and speedy type,” says Lilly. “I did some eventing on him but then fell in love with the idea of taking him pony racing, which mum was dead against. She said I’d blow his brain and wouldn’t be able to do a nice dressage test on him.
“Anyway, mum came around to the idea and I rode him in a pony race at Cheltenham and won. A few days late,r I did a one-day event on him and we lead the dressage and won the event.”
From that day on, Lilly’s mum allowed her to continue pony racing, and her next pony, Mr Bojangles, was a superstar in the pony racing ranks.
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“Mum was really good at allowing me to do pony racing training days and giving me the opportunity to learn more about racing – that’s when I got the bug for it,” explains Lilly. “It was at that point I decided I wanted to give point-to-pointing a go.”
Lilly bought her first pointer, Marblehead, from the same people who owned Mr Bojangles and she kept him with prolific point-to-point jockey and trainer Claire Hart. Lilly rode in her first point-to-point in February 2015 and scored her first win between the Flags in April 2016.
“I rode out for Richard Phillips locally to home while I was at school – I’d get dropped off there in the mornings and then walk up to Claire’s in the afternoon to ride out at hers,” she says. “I also rode out for Nigel Twiston-Davies some Saturdays too.”
Lilly Pinchin: “I pulled myself out of education’
Lilly decided school “wasn’t for her” at the age of 15.
“I went to the headmaster’s office at the end of a school day and told him I didn’t want to be at school anymore and literally pulled myself out of education,” she says. “In the car mum was like; ‘what on earth have you done, Lilly?’.”
But Lilly had made her mind up.
“I said ‘Look, mum, I’ve spoken to the racing school in Newmarket and I can do my English and maths GCSEs while I do a course there’”. And that’s exactly what she did.
At the age of 16, Lilly went to work for Fergal O’Brien.
“I rung Fergal up and said that I really wanted a job in racing. He told me to go to his with my mum and we sat down and chatted about it. He said to mum, ‘it’s hard work but if she can stomach it, she’ll be fine’.
“Fergal got me going on a lovely horse called Creevytennant, who provided me with my first winner against professionals under Rules – that horse really got my career off the ground.”
That winner was in May 2017 and to-date, Lilly has recorded 57 winners under Rules.
She moved on to work and ride for Graeme McPherson, where she rode as a conditional jockey.
“Graeme said that if I could ride five winners for him before December that season, that would be great. I ended up riding 14 winners for him that season – 2020/21 – and then in April 2021, I broke my back in a racing fall. I fracturing seven vertebrae, two ribs and had a little break of a bone in my neck. I was out for six months and it was tough.”
But Lilly kept herself busy in that time – she is a self-confessed animal lover, with a menagerie of pets at home, including Trev the territorial turkey, who has quite a following on social media.
“I love my animals and always have done – I’d always wanted my own turkeys and one day Cathy Twiston-Davies offered me some unhatched turkeys. I told mum they were hens, but then they hatched and grew. Mum wasn’t impressed.
“The fox took all but one of them one day – I thought he’d taken all of them until I found Trev alive and well two days later. He’s a real character.”
During her time on the sidelines, Lilly also did an online midwifery course.
“I’m not fully qualified as a midwife, but it’s something I’m interested in and I would love to pursue a career in it once I’m finished racing in the future,” she says.
Making a comeback
Lilly managed to ride a winner on just her second ride back from injury and she soon took advantage of her next opportunity, riding for Richard Hobson in France.
“That was an amazing experience. Richard rode out with us every day in France and he helped improve my riding massively,” she explains. “I rode nice horses in good races and that filled me with confidence and really helped me get going.
“Richard then said I should go and ride for a trainer back in Britain, which is when I rung Charlie Longsdon. I thought if I could ride out for him, maybe some race rides would pop up.”
Indeed Lilly did get a ride for Charlie, and she made it a winning one aboard Freethinker in a race at Newcastle in February 2022.
“I had a few more rides with some winners, then Charlie turned around at the start of the summer and asked me if I wanted a job riding for him full-time. I couldn’t say no – they are such a fantastic team.
“The Longsdons are great fun and have provided me with lots of opportunities, plus he obviously has lovely horses and really supportive owners.”
So what does Lilly credit her personal best season to?
“Being associated to a yard with plenty of firepower and my time with Richard, who as I’ve said, improved my riding a great deal,” she explains.
When she started out, Lilly Pinchin says she had three dreams she wanted to achieve; riding for The Queen – “that was amazing and I’m pretty sure I’m the only female to have ridden over fences for The Queen – plus I wanted to ride for Sheikh Fahad [of Qatar Racing], which I’ve managed and also to ride for JP McManus, which I’m booked to do this weekend. Riding for those high profile owners is incredible.”
High praise
Legendary former jockey Ruby Walsh recently praised Lilly’s riding on ITV Racing – how does Lilly take positive feedback like this?
“I don’t take compliments very well,” she laughs. “I think if he’s saying those sorts of things, it means I’m doing nothing wrong. Still, I need to improve on a few things and I’m sure there will be a race that Ruby analyses in the future where he spots something that I could have done better. But, yeah, it’s great, and it really does help you as jockey to hear that sort of positive reinforcement. Even if you’re sat there criticising yourself, listening to comments like that really does help with your riding and your confidence.”
There’s one goal that Lilly is desperate to achieve.
“I really want to ride out my claim,” she says, referring to the fact that when a jump jockey starts out their career, they can claim up to 10lbs, taking 10lbs off a horse’s given race weight. This weight allowance helps young jockeys get opportunities to ride despite having less experience. Lilly currently claims 3lbs – a claim she will lose once she has ridden 75 winners. At this point she will transition from a conditional jockey to fully professional. At the moment, she has just 17 more winners to ride before she achieves this ambition.
“From then on, I just want to ride as many winners as I can.”
From where we’re sitting, we don’t think it will be long at all until Lilly waves her conditional weight allowance goodbye.
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Former web features editor, point-to-point editor and digital racing editor
Gemma is an experienced journalist, who was a member of H&H staff from 2014 to September 2025. She is passionate about all equestrian sports, including racing and point-to-pointing. She has enjoyed riding out for top trainers Nicky Henderson and Charlie Appleby and took part in a charity Flat race at Epsom in August 2018. Gemma’s has reported from numerous five-star events around Britain and Europe, as well as European championships.
