Born in Ballinderry, near Tuam, County Galway, on July 3, 2000, Rossa Ryan is the son of former National Hunt trainer David Ryan. Prolific on the pony racing circuit in his native land, Ryan rode his first winner under Rules, Solar Heat, trained by Dot Love, in an apprentice handicap at Dundalk on December 9, 2016, while still apprenticed to his father. He subsequently crossed the Irish Sea to become apprenticed to Richard Hannon in Herridge, Wiltshire and rode his first winner on British soil, Willwams, trained by Hannon, in a claiming stakes race at Lingfield on March 17, 2017.
Ryan rode 21 winners in his first season with Hannon and in 2018 increased his seasonal tally to 78 winners, riding out his claim and finishing runner-up, behind Jason Watson, in the apprentice jockeys’ championships. On August 24, 2019, he rode his first Pattern winner, Duke Of Hazard, trained by Paul Cole, in the Celebration Mile at Goodwood. On July 15, 2020, he won a handicap at Yarmouth on Mr. Kiki, a quirky customer owned by Amo Racing, under the auspices of Kiavash Joorabchian, and trained by Ralph Beckett in Kimpton, Hampshire. A week later, he was offered, and accepted, a retainer by the influential owner – which would last for two years – and the job as first jockey to Beckett.By that stage, Ryan had already ridden his first Royal Ascot winner, Highland Chief, another for Paul Cole – who, by that stage, had been joined on his licence by his son, Oliver – in the Golden Gates Handicap on June 18, 2020.
He rode over 100 winners in a season for the first time in 2021, and, in 2023, rode his first Group 1 winner, Shaquille, trained by Julie Camacho, in the July Cup at Newmarket on his way to riding over 200 winners in a season for the first time. Ryan rode 201 winners in 2024 and, on October 3, 2025, reached the milestone of 1,000 winners on British soil on Blazeon Five, trained by Alan King, in a handicap at Ascot en route to a seasonal tally of 179 winners. Of his achievement, he said: “It’s great to have ridden 1,000 winners. I’ve had a lot of great support from people; I think the biggest thing is that I have a fantastic agent behind me. All the credit goes to Steve Croft. At the time of writing, Ryan has ridden four Group 1 winners to his name, including Bluestocking, trained by Beckett, in the Prix de l’Arc de Triomphe at Longchamp in 2024.