A History of Cheltenham Gold Cup Winners

As this year’s Cheltenham Gold Cup draws ever closer, familiarise yourself with the past winners of one of the most coveted prizes in all of horse racing.

The Cheltenham Gold Cup has been one of horse racing’s premier events for over 100 years. Taking place at the iconic Cheltenham Racecourse, it puts horses through a steeplechase involving 22 jumps across more than 5km. With the 2025 Cheltenham Festival drawing closer, we’re looking back at the Cheltenham Gold Cup’s past winners.

Who are the last ten Cheltenham Gold Cup winners?

Below, see the Cheltenham Gold Cup winners list of the last ten years, between 2015-2024.

Who are the most successful horses in Gold Cup history?

Cheltenham has hosted some of the best racehorses in the history of the sport, with 1941 runner Poet Prince managing the best-ever time around the course – finishing the race in just 6 minutes and 15 seconds.

There are nine horses who have won the Gold Cup more than once, with the most recent double-winner (Galopin des Champs) winning consecutive races in 2023 and 2024. Here are the most prolific winners in Gold Cup history:

1. Golden Miller (5-time Gold Cup winner)

From 1932 to 1936, the Irish Throroughbred Golden Miller broke a record that hasn’t been touched since, winning five consecutive Gold Cup races. Incidentally, the only horse in history to have won both the Gold Cup and the Grand National in the same year. His best time, six minutes and thirty seconds, was recorded during his fourth victory in 1935.

Best Mate (3-time Gold Cup winner)

Best Mate, an Irish-bred and English-trained thoroughbred, won back-to-back Gold Cups from 2002 to 2004. His 2003 race was his fastest, finishing with a time of six minutes and thirty nine seconds. Throughout his racing career, Best Mate famously never fell at a hurdle, and finished in first or second place in all 22 of his starts before his sudden death at the Haldon Gold Cup in 2005.

=2. Cottage Rake (3-time Gold Cup winner)

Another of the most decorated Cheltenham Gold Cup past winners, Cottage Rake achieved a hat-trick of wins between 1948 and 1950. His best time (six minutes and thirty six seconds) came in 1949, making him the first multiple-time winner since World War II halted the race.

=2. Arkle (3-time Gold Cup winner)

 The 1960s at Cheltenham were defined by Arkle’s run of dominance, winning three consecutive Gold Cups from 1964 to 1966. In 1965, Arkle earned his best time, finishing in six minutes and forty one seconds, which prompted odds of just 1/10 a year later – making him the shortest-priced winner in history, in 1966.

Which other horses have won multiple Gold Cups?

Other horses with multiple wins include Al Boum Photo and Galopin des Champs, who both won two races each in the last ten years. Here’s the full list of two-time Gold Cup winning horses:

·        Easter Hero (2)

·        Al Boum Photo (2)

·        L’Escargot (2)

·        Kauto Star (2)

·        Galopin Des Champs (2)

 Who are the most successful trainers in Gold Cup history?

A horse’s trainer can make all the difference in how they perform, and some have been much more successful than others. Here’s the list of Cheltenham Gold Cup winning trainers with the most victories to their name:

1. Tom Dreaper (5)

With five Cheltenham Gold Cup wins under his belt, Tom Dreaper holds the record as the most successful trainer in the event’s history. His first winning horse, Prince Regent, won the race in 1948. Sixteen years later, his horse Arkle would go on a run of dominance from 1964 to 1966, winning three Gold Cups in a row. He earned a fifth victory in 1968 with Fort Leney, before retiring in 1971.

=2. Vincent O’Brien (4)

With four Gold Cup wins to his name, Vincent O’Brien ties with four other trainers to rank as the second most successful in the competition’s history. Although he is best known for leading Cottage Rake to three successive wins between 1948 and 1950, he earned a fourth victory when Knock Hard took first place in 1953. Curiously, he also won three Grand Nationals in a row from 1953 to 1955 – each victory with a different horse.

=2. Willie Mullins (4)

One of the best trainers in recent horse racing history, horses trained by Willie Mullins have won four of the last six Gold Cups. His first two wins were with Al Boum Photo, earning consecutive victories in 2019 and 2020. In 2023 and 2024, Galopin des Champs took his total number of winners to four. With Galopin des Champs on the line once again for the 2025 race, he has a chance of equalling Tom Dreaper’s record.

=2. Fulke Walwyn (4)

After retiring as a jockey in 1939, Fulke Walwyn became one of the 20th century’s best trainers, leading four different horses to Gold Cup wins across three decades. His first victor in 1952 was Mont Tremblant, but it would take ten more years for him to earn a second win with Mandarin in 1962. Mill House’s win in 1963 made him a back-to-back winner, before The Dikler earned him his fourth win in 1973.

=2. Paul Nicholls (4)

Paul Nicholls’ first Gold Cup winning horse, See More Business, earned him a victory in the 1999 race. It was his winning streak in the late 2000s that would earn him a spot among the greats, though, as his horses won three consecutive races. Kauto Star’s victory in 2007 kickstarted his reign, before Denman gave him a third win in 2008. Finally, Kauto Star won the Cheltenham Gold Cup race again in 2009 to take Nicholls’ total wins to four.

=2. Basil Briscoe (4)

From 1932 to 1935, Basil Briscoe trained Golden Miller to four of his record-setting five consecutive wins, making him one of the most successful trainers in Gold Cup history and the first to earn four victories.

Which other trainers have won multiple Gold Cups?

Other successful trainers include Henrietta Knight, who trained Best Mate to three consecutive wins in the early 2000s, and Owen Anthony, whose training history includes a 1936 win with Golden Miller. Here is the full list of multiple-time winning trainers:

·        Henrietta Knight (3)

·        Owen Anthony (3)

·        Dan Moore (2)

·        Fred Rimmel (2)

·        George Beeby (2)

·        Henry De Bromhead (2)

·        Ivor Anthony (2)

·        Jack Anthony (2)

·        Jenny Pitman (2)

·        Nicky Henderson (2)

·        Noel Chance (2)

·        Peter Easterby (2)

Who are the most successful jockeys in Gold Cup history?

Past winners of the Cheltenham Gold Cup have included some of the biggest names in horse racing, but only the best jockeys have been able to earn multiple wins. Here are the most successful jockeys in the history of the Cheltenham Gold Cup:

=1. Pat Taaffe (4-time Gold Cup winner)

Pat Taaffe’s winning partnership with trainer Tom Dreaper led him to four total Gold Cup wins in his career, most notably when he rode Arkle to win three consecutive events in the 1960s. His fourth win came with another Dreaper-trained horse, Fort Leney, in 1968.

=1. Paul Townend (4-time Gold Cup winner)

The last few winners of the Cheltenham Gold Cup have seen Paul Townend solidify himself as one of the best jockeys in the history of the event. With two consecutive wins riding Al Boum Photo in 2019 and 2020, followed by his recent back-to-back wins on Galopin des Champs, his racing of Willie Mullins-trained horses has seen him equal Taaffe’s record, with a chance to beat it in 2025.

=3. Jim Culloty (3-time Gold Cup winner)

As the rider of fan-favourite Best Mate, who won a hat-trick of Gold Cups from 2002 to 2004, Jim Culloty became the first jockey of the 21st century to take home three titles. In fact, he was the first rider since Taaffe to win the event thrice in succession.

=3. Dick Rees (3-time Gold Cup winner)

The winner of the first ever Cheltenham Gold Cup in 1924, Dick Rees, led Red Splash to victory against 5/1 odds. He would earn two more wins by the end of the decade, with Patron Saint in 1928, and Easter Hero in 1929, making him the first rider to win multiple races in the event’s history.

=3. Aubrey Brabazon (3-time Gold Cup winner)

Aubrey Brabazon became the first jockey to win three consecutive Gold Cups from 1948 to 1950, when he led Cottage Rake to his run of dominance. He remains one of the most prolific winners in Cheltenham Gold Cup history to this day.

Which other jockeys have won the Gold Cup multiple times?

Twelve other jockeys have rode horses to multiple Gold Cup titles, including Gerry Wilson, who led Golden Miller to back-to-back wins, and BBC Sports Personality of the Year winner Tony McCoy. Here are the jockeys who have won two Cheltenham Gold Cups in their careers:

 ·        Tony McCoy (2)

·        Ted Leader (2)

·        Ruby Walsh (2)

·        Richard Johnson (2)

·        Mark Dwyer (2)

·        Jonjo O’Neill (2)

·        Gerry Wilson (2)

·        Fred Winter (2)

·        Evan Williams (2)

·        Connor O’Dwyer (2)

·        Bobby Beasley (2)

·        Barry Geraghty (2)

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