The 2025 Cheltenham Festival is set to get underway on Tuesday next week, and anticipation is building for another four days of top-class National Hunt racing. For jockeys, winning at Cheltenham is a career-defining achievement, with victories in the marquee races – such as the Gold Cup, Champion Hurdle, and Queen Mother Champion Chase – cementing their place in racing history.

 

Yet, a select few have gone beyond simply winning; they have dominated the event for sustained periods of their respective careers, forging a legacy that will be remembered for generations.

 

As we gear up for another thrilling edition of Cheltenham, it’s a fitting time to pay homage to some of the greatest jockeys who have graced this iconic meeting. Their enduring legacy continues to inspire the riders of today, who are on course to join them among the all-time greats.

Ruby Walsh – 59 Cheltenham Festival Wins

When it comes to Cheltenham Festival legends, one name stands above all – Ruby Walsh. With an astonishing 59 wins, he remains the most successful jockey in the Festival’s history. His dominance at Prestbury Park was such that he was crowned Leading Jockey at the meeting eleven times, including twice achieving a remarkable seven wins across four days.

 

Walsh’s most memorable Cheltenham triumphs include:

 

• Two Cheltenham Gold Cups (Kauto Star, 2007 & 2009)
• Four Champion Hurdles
• Three Queen Mother Champion Chases

 

He also holds the incredible record of being the first jockey to ride four winners in a single day at the Festival, a feat he achieved in 2017. Walsh’s partnership with Irish trainer Willie Mullins saw him guide some of the most famous horses in Festival history to victory, including Hurricane Fly, Faugheen, Douvan, and Annie Power.

 

Even in retirement, Walsh’s influence on Cheltenham remains strong. His insights as a racing pundit continue to shape discussions around the sport, and his record-breaking tally still stands as the benchmark for aspiring jump jockeys.

Barry Geraghty – 43 Cheltenham Festival Wins

Close behind Walsh’s legendary status is Barry Geraghty, who amassed 43 Festival victories during his glittering career. A supremely talented and adaptable rider, Geraghty became Leading Jockey at Cheltenham twice, most notably in 2003 when he rode five winners, setting a record at the time. He repeated the feat in 2012, once again being crowned the Festival’s top rider.

 

Geraghty’s most notable wins at Cheltenham include:

 

• Two Cheltenham Gold Cups (Kicking King, 2005 & Bobs Worth, 2013)
• Five Queen Mother Champion Chases
• Four Champion Hurdles

 

His final Champion Hurdle victory came in 2020 aboard Nicky Henderson’s Epatante. This moment underlined his class and ability to deliver on the biggest stage time and time again as he neared retirement. Having called time on his career shortly after, Geraghty remains one of the Festival’s most respected figures.

Sir AP McCoy – 31 Cheltenham Festival Wins

When discussing the greatest National Hunt jockeys, Sir AP McCoy is a name that always comes up. The 20-time Champion Jockey was a relentless competitor, and his 31 victories at Prestbury Park solidified his place among the all-time greats.

 

McCoy was crowned Leading Jockey at Cheltenham twice, in 1997 and 1998, and his biggest wins at the Festival include:

 

• Two Cheltenham Gold Cups (Mr Mulligan, 1997 & Synchronised, 2012)
• Three Champion Hurdles
• One Queen Mother Champion Chase

 

McCoy’s success wasn’t just about talent – it was about sheer determination and unwavering resilience. His fearless riding style and unmatched work ethic made him a favourite among punters and trainers alike. His 2012 Gold Cup victory aboard Synchronised remains one of the most emotional and inspiring moments in Festival history, showcasing his ability to produce career-defining rides on the grandest stage.

Pat Taaffe – 25 Cheltenham Festival Wins

Few jockeys have left an imprint on Cheltenham quite like Pat Taaffe. Though he rode in a different era, his 25 Festival wins remain an astonishing achievement. With most of his victories coming in steeplechases – 22 of them, to be exact- he holds a higher win percentage than any other Festival jockey.

 

Taaffe’s most iconic moments came aboard the legendary Arkle, with whom he secured three consecutive Gold Cup victories in 1964, 1965, and 1966. Even after Arkle retired, Taaffe wasn’t done – he won the Gold Cup again in 1968 with Fort Leney. He shares the record as the jockey with the most Gold Cup wins (four) alongside Paul Townend.

 

His ability to judge a race and time his challenge to perfection made him one of the finest riders of his generation. More than 30 years after his passing in 1993, only a handful of jockeys have surpassed his Cheltenham tally – a testament to his enduring legacy.

Richard Johnson – 23 Cheltenham Festival Wins

Another jockey who made a lasting impact on the Cheltenham Festival is Richard Johnson. With 23 Festival wins, Johnson was a model of consistency, winning all four of the championship races at least once.

 

His most celebrated triumphs include:

 

• Two Cheltenham Gold Cups (Looks Like Trouble, 2000 & Native River, 2018)
• One Queen Mother Champion Chase (Flagship Uberalles, 2002)
• One Champion Hurdle (Rooster Booster, 2003)

 

His Gold Cup win on Native River in 2018 was one of the Festival’s great moments – a thrilling battle in testing conditions where Johnson’s tactical nous and stamina came to the fore. His legacy at Cheltenham is defined by his sheer resilience and commitment to the sport, making him one of the most respected figures in National Hunt racing.

Who Could Join the Cheltenham Greats?

While the legends above have already secured their places in history, the current generation of jockeys is looking to carve out their legacies at the Festival. Riders such as Paul Townend, Rachael Blackmore, and Nico de Boinville are all adding to their growing lists of Cheltenham victories.

 

• Paul Townend already ranks third in the all-time victories list at the age of 34, with the same number of Cheltenham wins, too. He has taken over as Willie Mullins’s stable jockey and won a joint-record four Gold Cups (2019, 2020, 2023, 2024). He is the bookies’ favourite for Gold Cup betting odds to take home a record-breaking fifth title riding Galopin Des Champs, which will cement his name into the long-standing prestige of the event.
• Rachael Blackmore made history in 2021 as the first female rider to be crowned Leading Jockey at the Festival and backed it up by winning the Gold Cup in 2022 on A Plus Tard – the first female jockey to have won the race.
• Nico de Boinville has already won multiple top races, including the Gold Cup (Coneygree, 2015) and Champion Hurdle (Constitution Hill, 2023). This year, he could add more winners to his 16-strong triumph list at the Festival.

 

With the 2025 Festival fast approaching, these riders will have another chance to add their names to the roll of honour and further challenge the records set by the legends before them.

Harry Bentley, 31, rode over 500 winners on British soil between 2009 and 2020, but found international fame in the Middle East, in the United Arab Emirates and, most notably, in Qatar. As second-choice rider to Qatar Racing, under the auspices of Sheikh Fahad bin Abdullah Al-Thani, he was Qatar Champion Jockey six times between 2013/14 and 2018/19. However, while wintering in Dubai in 2020, Bentley received an unexpected offer of a contract in Hong Kong and, in his own words, ‘…it just seemed right to give it a go’.

Bentley began riding, full-time, in Hong Kong in April 2021 and, after just five winners in his debut season in the jurisdiction, increased his seasonal tally to 25 winners in both 2021/22 and 2022/23. He has also made strong start to the 2023/24 campaign, riding a further seven winners but, on November 3, 2023, he was, rather mysteriously, stood down from riding in races, barrier trials and trackwork by the Hong Kong Jockey Club (HKJK). Bentley was subsequently charged with, and plead guilty to improper conduct, leading to a two-month suspension, until January 3, 2024, and a fine of HK$300,000, or £31,379.

Bentley admitted to what the HKJK called ‘improper communication’ with a unnamed individual, who provided him with a private phone for the purpose, insofar as he passed on information about horses he was riding in return for potential payment, although any such payment did not, in fact, materialise. Despite his guilty plea, he told the ‘Racing Post’, ‘I want to be extremely clear that this charge is in no way related to giving tips, betting, wagering, race-fixing or accepting payment ahead of race-riding.’ He also stated that the charge related to ‘an isolated incident’.

The 2023 Breeders’ Cup as staged at Santa Anita Park in Arcadia, California on November 3 and 4, but one notable absentee from the end-of-season showcase meeting was Hollie Doyle. Having ridden over a hundred winners on British soil for the fifth calendar year running and finished fifth in the Flat Jockeys’ Championship, 13 winners adrift of her husband, Tom Marquand, the ‘Pocket Rocket’ was originally booked to ride Bradsell, trained by Archie Watson, in the $1 million Breeders’ Cup Turf Sprint.

Bradsell had secured an automatic berth in the Breeders’ Cup Turf Sprint by virtue of a narrow victory over subsequent Prix de l’Abbaye de Longchamp winner Highfield Princess in the Group 1 King’s Stand Stakes at Royal Ascot on June 20, which was part of the ‘Breeders’ Cup Challenge Series: Win and You’re In’ program. However, on October 16, Doyle fell foul of the stewards at Kempton Park and was handed a seven-day suspension for careless riding on her mount, Rose Light, trained by Jonathan Portman, in the penultimate fillies’ handicap.

Early in the middle-distance contest, Doyle was adjudged to have allowed Rose Light to drift right when insufficiently clear of Flying Circus, ridden by Neil Callan – who was badly hampered and eventually finished last – and causing a ‘knock on’ effect, which affected three other riders. The suspension, which was due to run from October 30 to November 4, plus November 6, was upheld on appeal and Doyle was denied the opportunity to ride her first Breeders’ Cup winner.

Doyle said that she was ‘naturally disappointed to miss the ride’ but, as events transpired, she did not miss anything. Bradsell worked at Santa Anita Park on November 1, but the following day Watson informed the local stewards that the Tasleet colt had been scratched from the Breeders’ Cup Turf Sprint and would not be taking his place in the field.

The adrenaline rush, the cheering audience and the atmosphere present during the English horse racing is something that has made its roots in the imagination of people for many centuries. The United Kingdom’s long and impressive history in riding encourages many different race tracks to go for such famous events elsewhere around the globe, which with every event, becomes more and more exclusive and traditions are emphasized. Every event has its own distinct and detailed lineage.

The Classic Calendar

Each season of the United Kingdom’s horse racing calendar is magical, serving as a fountainhead of unlimited fanatical joy. Just like the rest of the events in the UK, these have the fanfare that comes along with competitions as well as social celebrations built around it. The major race meets work like slots to gambling enthusiasts, capturing the utmost energy and anticipation for the days of the races.

Royal Ascot: The Crown Jewel

Each year, the Royal Ascot Festival is acclaimed as one of the best and most distinguished. During these five days in June, the region of Berkshire transforms into an extraordinary mix of sport and fashion.

As is customary, a large number of participants take part in wagering, but the focus is on the dopes, where a blend of the ancient style with the most up-to-date sort of racing offers an action-packed show. The Royal Procession also kicks these events off, which is a remaking of a ritual that began in 1711. It is headlined by the aristocracy arriving on Horseback, bedecked in exquisite coaches.

The Grand National: Liverpool’s Legacy

The Grand National at Aintree confirms that in the contest of horses and riders, all facets of human and animal capabilities get stretched, and the winner is not always the one to cross the finish line first.

While other riders claim to be great, the most famous and perhaps the hardest contest of all steeplechase, which is four miles long with thirty jumps, is at Aintree. Unlike Ascot, Aintree has an even deeper and more classical form of racing at one of the finest places in the UK. The atmosphere is full of a sort of feral excitability that brings to mind the ultimate delight of the game.

The Epsom Derby: History in Motion

Separated from the other five British Classics is The Derby held at Epsom Downs. It is considered by many to be the most prestigious of the five. Every June, the usually serene Surrey downs metamorphose into a racing spectacle. This unique test of skill has challenged the best three-year-olds since 1780 with its difficult gradients and sharp turns, producing legendary names in racing history.

Cheltenham Festival: Jump Racing’s Finest Hour

March is when the Cheltenham Festival is held and features this national event. It is the premier event of the National Hunt racing calendar. A major highlight of the Festival is the “Cheltenham Roar,” which generally occurs upon celebration during the start of the races, and fans’ adrenaline boosts their stamina.

Other than that, the grand finale day of the festival represents the highlight of the gold cup race, where the fiction book-like eloquence of equestes brushes over all the listeners.

York’s Ebor Festival: Northern Charm

The people of Yorkshire blend their famous hospitality with the top horse racing in the world during the Ebor Festival held at York Racecourse. This coming together in August has a historical note with it which has spectacularly transformed this event into one of it’s international multi-racing entirely differently and beautifully. Horses of the highest class form all corners of the globe participate in the Juddmonte International race that is hosted at the York Racecourse which is famous for top level racing.

Glorious Goodwood: A Summer Spectacle

The Glorious Goodwood event includes five major racing competitions of the season. It’s celebrated under the shimmering sun in the hills of Sussex Downs. In the horse racing world, the Qatar Sussex Stakes is one of the most well-known mile races of the summer season, and its grade one is elevated above the rest. The hilly course also adds an appealing challenge to the mounted athletes.

In Closing

It is clear that we ought to remember that these are major events of the year and in reality, contain a lot more than just sports as they showcase British culture, customs, and even the grandeur of the nation.

The beauty of Royal Ascot and the Aintree Grand National’s spectacular showpiece chase is bound to give you a taste of the sport in a way only these horse racing events can provide. If horse racing is your cup of tea, this is an opportunity of a lifetime, as these events are guaranteed to give you the experience that justifies why horse racing is said to be the sport of kings.

The race’s highlight is the illusive factors. These, combined with superb execution, clothing appropriate to the occasion, and the specific historical period during which the events seek to capture the people’s imagination, ensure that the performances are literally unforgettable. All sports aficionados surely have every single one of the events listed on their calendars.