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The champion apprentice jockey contender reached the milestone moment of “losing his claim” at Listowel last month by riding two winners for trainer Gavin Cromwell.

Victories aboard Secret Force and Flying Fortress at the Co. Kerry track took Whearty to and beyond the 95-winner mark required for an apprentice jockey to no longer claim a weight allowance.

“[It was a] great day for the boss, Gavin. I’ve been getting the rides and the support, so hopefully, that’ll continue,” said Whearty.

The Bellewstown native rides out of Cromwell’s yard after he spent his formative years around his father’s horses at home in Co. Meath.

From there, Whearty furthered his craft at riding school and engaged in hunting and showjumping.

But racing ponies is what kickstarted Whearty’s love affair with the sport and the rest, he says, is now history.

He said: “I did a pony race and got some good experience and eventually ended up at Gavin’s yard. I’ve never looked back since.

“It’s a great yard, very progressive. Gavin uses everyone who comes in and works hard, you usually get rides. He’s always trying to build the place up, and it’s a unique facility. Onwards and upwards for him.

“When you get the opportunities, you have to take them with both hands. There are very few double meetings, so when the chances come, you really have to make the most of them.

“The horses you get on can push you to the next level."

Treasured Royal lands the opener at @NavanRaces, the Irish EBF Auction Series Fillies Maiden, for Robert Whearty and trainer Gavin Cromwell pic.twitter.com/98SZlFhFZP

— Horse Racing Ireland (@HRIRacing) September 6, 2025

Cromwell has not just provided Whearty with opportunities to ride; he has also given him the chance to immerse himself around and learn from experienced jockeys such as six-time Cheltenham winner Keith Donoghue and Grade 1 winner Kevin Sexton.

Picking the brains of some of the most established names in the game and being supported by them is something that Whearty believes has helped him develop.

He added: “We’ve got great riders in the yard. It’s a good team to lean on for advice. There’s a lot of talent there. A lot of people are willing to help if you ask, and that’s been very supportive for me."

Whearty described the standout moment of his career to date as his sensational victory riding Big Gossey to land the Bold Lad Sprint Handicap at 16-1 during the Irish Champions Festival at the Curragh in 2023.

That triumph is one of four he has celebrated when teaming up with the grey gelding; a horse he has called a “legend” in the past.

“That was a great moment, probably one of the best I’ve had in racing. Hopefully, there’ll be more days like that,” Whearty said.

Whearty had a lot of inspirational jockeys to look up to growing up and revealed it is hard for young riders to do anything else than try to mimic their heroes.

He continued: “I suppose AP McCoy and Ruby Walsh are the obvious ones [I watched growing up]. I’ve always looked up to Kieren Fallon as well. I admired Sea The Stars, and Frankie Dettori, of course, is another big one.

“You try to model your style after them, take bits from their riding, and tidy up your own style as best you can."

With winter on the horizon, the world is Whearty’s oyster, and he has made no secret of his ambition to travel the world and expand his horizons even further.

He added: "I’d love to go off and experience different parts of the world. There are places like Dubai, Australia, and America that I’d love to visit and ride in.

“As for ambitions for the rest of the season, I just want to build up new contacts and ride as many winners as possible before the season ends.”