Cheltenham Festival-winning trainer makes international showjumping debut: ‘It’s been great – you never know, I might have another go...’

“It’s something I’ve always wanted to do,” says Oliver Greenall, as we stand ringside at Bolesworth International, presented by Al Shira’aa.

The racehorse trainer, who holds a joint licence with Josh Guerriero and saddled Iroko to finish fourth in the 2025 Grand National, dipped his toe into the world of showjumping with a solid international debut in Bolesworth’s amateur classes aboard O’Balou De Bourguignon.

“I’ve only recently started showjumping, so it was all a bit daunting the first week – I was making mistakes and we kept having fences down – but this week has been loads better,” says Oliver.

In classic sportsman style, he is already mulling over where he could improve. But to go from never really having showjumped – at least not since he was a child – to jumping in 1.15m classes at a major show in a short space of time is no easy feat.

“I think we’re both quite mentally and physically tired now,” says Oliver, at the end of his second week of jumping, which included ninth place with a clear round in Thursday’s Peel Port Logistics speed class.

“It’s been a long couple of weeks, but it’s been great, a really good experience. I’m so glad I’ve been able to do it, you never know, I might have another go…”

Oliver, who had success as amateur jockey before taking out his training licence, is based a stone’s throw from the show and has been helping Bolesworth director and showjumper Nina Barbour prepare for the Magnolia Cup charity race at Goodwood this month.

“Showjumping has always been something I wanted to have a good go at. I got this horse from Anthony Condon to have as a riding horse at home,” he says, explaining that the pair are great friends and Anthony, who won the CSI3* grand prix on Bolesworth’s first week, has been nudging him to have a go.

“Nina has been coming to ride at the yard and she said, ‘Well, why don’t you come and do Bolesworth?’ I’ve been for a load of lessons, did two little shows beforehand – fitting those in alongside racing – and then I came here.

“The first day the horse was really spooky, then ever since then, he’s been absolutely brilliant. He’s a real, safe, schoolmaster, and so chill. At home, I jump rails and hedges with him, he’s brilliant.”

He adds: “I’m learning; every time I jump, Anthony adds something else, ‘You need to go a bit tighter, you need to look at the clock, you need to learn the strides’. You think you’re getting it and then there’s more to learn. I never really appreciated how technical and difficult it really is, the margins are so fine.

“Being local, friends and family have come to watch. It’s been an amazing experience.”

It’s been a busy fortnight – alongside showjumping, the yard has had runners across the country, and Oliver has been back and forth to France for sales. The day job doesn’t stop, although for Iroko, it is still summer holiday season.

“He’s in good form,” says Oliver. “He’s still in Ireland at Martinstown on his holidays with [2025 Cheltenham Festival winner] Jagwar, but he’ll be coming back any day and the plan is to go back to the Grand National with him.”

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