Willie Ryan

Born in Cambridge on December 22, 1964, William ‘Willie’ Ryan is the son of Denis Ryan, who won the Chester Vase on Articulate in 1956 while still an apprenticed. Ryan Jnr. became apprenticed to Reg Hollinshead, renowned for his ‘academy’ for young jockeys, in Upper Longdon, Staffordshire, and rode his first winner, Will George, at Windsor on August 23, 1982. Three years later, in 1985, he followed in the footsteps of fellow Hollinshead alumni Steve Perks and Kevin Darley by becoming champion apprentice, sharing the title with Gary Carter on 37 winners apiece.

Later in his career, Ryan became an integral part of the operation at Warren Place, Newmarket, home of eventual 10-time champion trainer Henry (later Sir Henry) Cecil. In his capacity as second jockey, he officially ‘won’ the St. James’s Palace Stakes at Royal Ascot on Perpendicular on June 16, 1992, but, having been beaten 1½ lengths, the Shirley Heights colt was awarded the race in the stewards’ room, with the first past the post, Kooyonga disqualified and placed third.

Nevertheless, Ryan was promoted to first jockey at Warren Place following the shock retirement of his predecessor, Steve Cauthen, at the end of 1992. He rode his first Group 1 winner for Cecil, King’s Theatre (who would later become a jumps sire of note), in the Racing Post Trophy at Doncaster on October 23, 1993 and his second, Benny The Dip, in the Derby on June 7, 1997.

For outside stables, he achieved further success at the highest level on Court Of Honour, trained by Peter Chapple-Hyam, in the Gran Premio Del Jockey Club Italiano at San Siro on October 15, 1995 and Iktamal in the Haydock Park Sprint Cup on September 7, 1996. Ryan retired from the saddle at the end of the 2004 season, having previously told the ‘Racing Post, ‘I feel that I’ve had my best days as a jockey and the right thing to do is to be honest with myself and the people I ride for.’

Oisin Orr

On June 3, 2022, the ‘Racing Post’ reported that Oisn Orr had been appointed stable jockey to Richard Fahey at Mews House in Musley Bank, Malton, Yorkshire, succeeding Paul Hanagan in that role. That season, he rode 41 winners on British soil, including Midnight Mile, trained by Fahey, in the Oh So Sharp Stakes at Newmarket and, in 2023, increased his seasonal tally to 64 winners, including several more high-profile victories. In 2024, so far, he has already ridden 46 winners, from 369 rides at a strike rate of 12%, and currently lies in ninth place in the Flat Jockeys’ Championship.

Originally from Rathmullan, Co. Donegal, Orr rode his first winner, Balmont Blast, trained by Edward Lynam, in an apprentice maiden race at Dundalk on January 23, 2015. He went on to become champion apprentice in his native land twice, in 2017, when he finished the season just one winner ahead of Killian Leonard, and in 2019, when he rode a double on the final day to share the apprentices’ title with Andrew Slattery. Orr reached the milestone of 95 career winners, thereby riding out his claim, on Anya Ylina, trained by Dermot Weld, in a fillies’ maiden at Gowran Park on the evening of May 29, 2019.

By that stage, Weld had already provided Orr with his first Listed and Group winner, Imaging in the Heritage Stakes at Leopardstown on Aoril 3, 2019 and the Group 3 Gladness Stakes at Naas ten days later. The following season, his first as a fully-fledged professional, Orr rode his first, and so far only, Group 1 winner, Search For A Song, trained by Weld, in the Irish St. Leger at the Curragh on September 13, 2020.

Twice named Donegal Sportstar of the Year, in 2020 and 2023, Orr has already spoken about how the switch to Britain has revitalised his career. Already with nine Group race victories to his name, at home and abroad, further success at the highest level on British soil is surely only a matter of time.

Leighton Aspell

Leighton Aspell retired from the saddle, for the second and final time, on February 23, 2020, after failing to complete the course on Ventura Dragon, trained by Oliver Sherwood, in a handicap hurdle at Fontwell. By that stage, he had ridden a total of 909 winners under National Hunt rules in Britain, but is best remembered for winning back-to-back renewals of the Grand National in 2014 and 2015.

On the first occasion, Aspell steered Pineau De Re, trained by Dr. Richard Newland, to a victory in the Aintree showpiece and said afterwards, ‘Even to get a ride in the Grand National is a great thing, but to get one with a live chance is even better.’ Little did he know that he would be presented with his next ‘live chance’ just 12 months later, in the form of another 25/1 chance, the doughty Many Clouds, also trained by Sherwood, on whom he had already won the Hennessy Gold Cup (now the Coral Gold Cup) at Newbury the previous November.

Born in County Kildare on June 12, 1976, Aspell moved from Ireland to Britain as a 16-year-old, where he followed in the footsteps of the likes of Pat Eddery, Kevin Darley and Walter Swinburn by becoming apprenticed to Reg Hollinshead at Upper Longdon, Staffordshire. He rode the first of his 11 winners on the Flat, Prime Painter, trained by Roger Fisher, in a four-runner apprentices’ handicap at Hamilton on May 26, 1993 and the last, C’Est No Mour, trained by Peter Hedegr, in the Jump Jockeys’ Derby Handicap at Epsom on September 14, 2017.

Always destined to become a National Hunt jockey, Aspell opened his account ‘over the sticks’ on Karar, trained by Richard Rowe, in a novices’ handicap hurdle at Huntingdon on May 17, 1995. Thereafter, he racked up aound 400 winners, with high-profile victories in the Swinton Handicap Hurdle at Haydock and the Welsh Grand National (twice), before announcing his shock retirement, aged 31, in July 2007. Having originally said that he ‘just wasn’t getting much of a kick out of it any more’, he joined John Dunlop as pupil assistant, but found the lure of the Grand National impossible to resist and was back in the saddle 18 months later.

Rossa Ryan

In 2023, Rossa Ryan enjoyed far and away his most successful season so far, numerically and fiscally, finishing the year with 202 winners from 1,090 rides at a strike rate of 19% and amassing over £3.6 million in total prize money. He was also a ‘punters’ pal’, accruing a healthy level stakes profit of £109.24. The vagaries of the Flat Jockeys’ Championship meant that, despite being the most prolific jockey in the country for the calendar year, he did not become Champion Jockey. Nevertheless, Ryan, who turned 24 on July 3, 2024, has continued the good work in the new season. At the time of writing, since the start of the Flat Jockeys’ Championship, on May 4, 2024, he has ridden 52 winners from 293 rides, at a strike rate of 18%, and currently lies third on the table.

Aside from passing the significant milestone of over 200 winners, 2023 was also a red-letter year for Ryan insofar that, on July 15, he rode his first Group 1 winner, Shaquille, trained by Julie Camacho, in the July Cup at Newmarket. Sadly, his first ride in the Derby proved less fruitful, with his mount, Macduff, trained by Ralph Beckett, only able to finish a distant thirteenth of 15 finishers, 29½ lengths behind the winner, City Of Troy.

Born and raised in Ballinderry, near Tuam, Co. Galway, Rossa Ryan is, of course, the son of trainer David Ryan. A graduate from pony racing, in which he was hugely successful, Ryan Jnr. Rode his first winner under Rules, Solar Heat, trained by Dot Love, in an apprentices’ handicap at Dundalk on December 9, 2016. The following January he became apprenticed to Wiltshire trainer Richard Hannon and, in 2019, finished runner-up in the apprentices’ title race. In 2020, Ryan accepted a retainer from Amo Racing, under the auspices of football agent Kia Joorabchian, and although that association came to an end in 2022 his career has continued to flourish.