From Ruby Walsh to Fred Winter, we rank the most successful jockeys in Cheltenham history and look at which riders will lead the way at this year's Festival.
Each year, Prestbury Park in Cheltenham plays host to the finest jockeys across Britain, Ireland, and even France. With numerous races throughout the weekend, there are plenty of chances for them to win big and etch their names in the history books, but which jockeys have the most Cheltenham wins?
Plenty of the Festival’s leading jockeys are retired, but some riders in our list are still among the Cheltenham betting favourites to be named Leading Jockey.
Read on to find out the most successful jockeys in Cheltenham history, or explore our Cheltenham races guide to find out all you need to know about the Festival.
The jockeys with the most Cheltenham wins
For a quick run-down of the best Cotswold competitors in history, here’s a summary of the top ten most successful Cheltenham jockeys of all time:
Ruby Walsh (59 wins)
Barry Geraghty (43 wins)
Paul Townend (38 wins)
AP McCoy (31 wins)
Pat Taaffe (25 wins)
Richard Johnson and Davy Russell (22 wins)
Richard Dunwoody and Rachael Blackmore (18 wins)
Fred Winter, Nico De Boinville, and Charlie Swan (17 wins)
More information about Cheltenham’s leading jockeys
Looking for a more detailed breakdown of the riders who made our list? Here are some facts about the most prolific winners in Cheltenham history:
1. Ruby Walsh
One of the most famous Irish jockeys of all time, Ruby Walsh, leads the pack when it comes to the most successful riders in Cheltenham history, with an astonishing 59 wins to his name. He won each of the four championship races – the Champion Hurdle, Queen Mother Champion Chase, Stayers’ Hurdle and Gold Cup – at least twice.
He is remembered for riding the legendary Kauto Star, but other greats he won on at Cheltenham include Hurricane Fly, Big Buck’s, Master Minded, Faugheen, Quevega and Annie Power.
2. Barry Geraghty
Barry Geraghty ranks in a very respectable second place with 43 Cheltenham wins under his belt. His last victory was in the 2020 County Hurdle, where he placed first on Saint Roi to mark his fifth win of that year’s Festival.
He won the Gold Cup on Kicking King and Bobs Worth, as well as the Champion Hurdle on Jezki and Punjabi. He is also famed for his partnership with two-time Champion Chase winner Moscow Flyer.
3. Paul Townend
One of the fastest-rising jockeys on our list is Paul Townend, who’s the highest-ranking active rider. After claiming a record-equalling four Gold Cup wins, with Al Boum Photo in 2019 and 2020, then Galopin Des Champs in 2023 and 2024, he became one of the most successful racers in modern Cheltenham history.
Townend has also ridden the likes of State Man and Energumene to glory at Cheltenham, with his total number of wins currently standing at 38. The Irishman shows no signs of slowing down, though, and he’ll be eyeing up any chance he can get to add to his collection.
4. AP McCoy
Britain’s record-breaking 20-time champion jumps jockey AP McCoy enjoyed 31 Festival winners across his illustrious career. He famously claimed victory in his final Cheltenham race, the 2015 Ryanair Chase, on Uxizandre.
He won the Cheltenham Gold Cup twice on Synchronised and Mr Mulligan and the Champion Hurdle three times – alongside the Ryanair, Arkle and Albert Bartlett Novices’ Hurdle.
5. Pat Taaffe
Pat Taaffe was one of the finest riders of his generation, with 25 Cheltenham Festival wins in an era with fewer races than there are now. He dominated in the 1960s, famously riding Arkle to three Cheltenham Gold Cup victories, before winning his fourth in 1968 on Fort Leney.
After retiring in 1970, Taaffe tried his hand as a trainer, although he never reached the same success that he experienced as a jockey. Still, his record as a rider remains one of the most impressive in the Festival’s history.
-6. Richard Johnson
Richard Johnson is the second-most prolific winner in National Hunt history, making him one of the most famous British jockeys of all time. Only his career rival, AP McCoy, has recorded more winners.
Johnson was no stranger to success at Cheltenham, having won each of the big four races before his retirement. After winning his first Gold Cup on Looks Like Trouble in 2000, he would have to wait 18 years before placing first in the event again, when he rode Native River to a win in 2018. In total, Johnson earned 22 Cheltenham wins.
-6. Davy Russell
Tied with Richard Johnson at 22 wins, Davy Russell was another of Cheltenham’s most successful jockeys at the peak of his career. His first winner was Native Jack, who placed first in the 2006 Glenfarclas Cross Country Chase. Russell would go on to claim a win in every Festival until 2019, eventually racing his final winner in 2020.
His biggest highlight was a 2014 Gold Cup on Lord Windermere, but with 22 Cheltenham winners, it’s hard to sum his legacy up in one race.
-8. Richard Dunwoody
One of the greatest jockeys of his era, Richard Dunwoody once held the record for the most National Hunt wins in history, before eventually being overtaken by McCoy and Johnson.
He had 18 Cheltenham winners, including the Gold Cup on Charter Party in 1988. He also won the 1990 Champion Hurdle on Kribensis, and landed the Arkle three times.
-8. Rachael Blackmore
The only female jockey to break into our top ten, Irish rider Rachael Blackmore turned the racing world on its head in the 2020s, before eventually announcing her retirement in 2025. Some of her most famous winners include Honeysuckle, who won consecutive Champion Hurdles and two David Nicholson Mares’ Hurdles, and three-time winner Bob Olinger.
By far Blackmore’s biggest accomplishment, though, was becoming the first woman to claim a Gold Cup. In 2022, she rode A Plus Tard to a historic victory in the event. Her 18 career wins put her on even footing with Dunwoody.
-10. Fred Winter
Fred Winter was one of the most successful jockeys of his generation, but he retired from riding in 1964 to become a trainer. He found fame in both roles, with 17 career wins as a jockey, including two Gold Cups and three Champion Hurdles. He also trained victors in both races, claiming 28 wins in the Cotswolds after changing his job title.
Winter was regarded as one of the best jockeys of his generation: the Fred Winter Juvenile Handicap Hurdle was inaugurated in 2005 in his honour.
-10. Nico de Boinville
British jockey Nico de Boinville has raced more Grade 1 National Hunt winners than any other rider currently active in the sport. His first win at Cheltenham came in 2015, when he led Coneygree to a first-place finish in the Gold Cup.
Since then, de Boinville has increased his winning record to 17. His partnership with trainer Nicky Henderson has seen him ride leading horses such as Altior and Constitution Hill.
-10. Charlie Swan
Finishing off our three-way tie in tenth place is Charlie Swan. Best known for riding Istabraq, the Irishman claimed the title of top jockey at the Cheltenham Festival twice, and he also reigned as the Irish National Hunt champion jockey for nine years.
Swan’s first Cheltenham win came in the 1990 Stayers’ Hurdle, but his three Champion Hurdle wins are arguably his defining achievement at the Festival. With 17 wins, he rounds out our top ten.
The leading jockeys at Cheltenham 2026
You’ll be able to catch some of the best Cheltenham jockeys of all time in action at the 2026 edition of the Festival.
Paul Townend, in particular, will have plenty of eyes on him as he aims to overtake Barry Geraghty in second on our ranking. With just five wins separating their records, he could claim a silver medal in our all-time list this year.
Nico de Boinville will also be looking to add more gold to his trophy cabinet. As one of the leading riders for legendary trainer Nicky Henderson, he’ll likely be riding top names like Constitution Hill and Jonbon.
It’s also worth looking out for some jockeys who haven’t placed on our list, but could be in for blockbuster years at Prestbury Park. Reigning British champion jump jockey Sean Bowen is yet to claim a victory at Cheltenham Festival, but has listed a Gold Cup win as his main career goal. Could 2026 finally be the year he breaks his streak of misfortune?
Irish jockey Harry Cobden is also expected to feature in many of Cheltenham’s biggest races this year. With 6 wins to his name already, including a victory in the 2025 Golden Miller Novices’ Chase, he’ll be looking to expand his portfolio in 2026.
Cobden was announced as the retained jockey of racehorse owner J. P. McManus at the start of 2026, but this won’t take effect until the Cheltenham Festival has finished. He currently rides many of Paul Nicholls’ horses.
The odds for all of the jockeys’ rides can be seen on Betway’s Cheltenham odds page. Additionally, for betting tips, strategies, and more information, check out our guide on how to bet on Cheltenham.
