Early years

The first horse race known as the Cheltenham Gold Cup took place in July 1819. It was a flat race, and it was contested over 3 miles on Cleeve Hill, which overlooks the present venue. The inaugural winner, Spectre, won a prize of 100 guineas for his owner Mr Bodenham.

The founding of the Cheltenham Gold Cup was an important event in the history of National Hunt racing. In the early 1920s there were very few valuable weight-for-age steeplechases. Apart from the National Hunt Chase at Cheltenham and the Champion Chase at Liverpool all the most important races were handicaps. Some people thought this was not in the best interests of the sport, so the Gold Cup was founded to redress the balance to a certain degree. It is not sure who had the idea for the Gold Cup, but it may have been Mr F.H. Cathcart, the Chairman of the Cheltenham Executive. It took a while for the prestige of the Gold Cup to grow, but it is now regarded as the true championship race for staying chasers.

The Cheltenham Gold Cup was first run as a steeplechase on 12 March 1924, over 3 miles 3 furlongs, for five year olds and upwards, with five year olds carrying 11 st 4 lbs, and the remainder 12 st. The race was covered by Pathe News.^[1] A prize of £685 was awarded to the owner of the winning horse. This was considerably less valuable than the National Hunt Chase, which was still regarded as the most important race of the meeting. The weather at Cheltenham for that first Gold Cup was mild and springlike. Among the spectators was the Prince of Wales, a friend of Harry Brown who was riding Conjuror II. There was an exciting finish, with Major E.H. Wyndham's five year old, Red Splash, 5/1, ridden by Dick Rees and trained by Fred Withington, beating Conjuror II by a head, with Gerald L a neck away third. Forewarned, ridden by Jack Anthony, was the 3/1 favourite. Red Splash appeared to have a great future, but he was difficult to train and never again ran in the Gold Cup. ^[2]

The event originally took place on what is now the "Old Course" at Cheltenham. In its early years it was overshadowed at the Festival by another race, the National Hunt Chase and was worth less in prize money than the County Handicap Hurdle which had a purse of £1,000.^[3]

The Gold Cup was abandoned in 1931 (because of frost) and 1937 (flooding), but the five intervening years saw the emergence of the most successful horse in the event's history. All five races from 1932 to 1936 were won by Golden Miller, who also won the Grand National in 1934.

During World War II, the Gold Cup was cancelled twice, in 1943 and 1944. The first multiple winner in the post-war era was Cottage Rake, who won the three runnings from 1948 to 1950. Cottage Rake was trained in Ireland by Vincent O'Brien, and his successes helped to popularise the Gold Cup, and the Festival itself, with the Irish public.

Modern era

The Gold Cup was switched to the "New Course" in 1959, and this remains the regular track used for the event. In the mid-1960s, the race was dominated by Arkle, who won three consecutive runnings from 1964 to 1966. Such was Arkle's perceived superiority before the last of these victories that he was given a starting price of 1/10 (a £10 bet would have won £1). He remains the shortest-priced winner in the race's history.

The first commercial sponsorship of the race was by Piper Champagne, which began supporting the event in 1972. The Tote (now known as Totesport) became the sponsor in 1980.

The most remarkable feat in the Gold Cup by a trainer came in 1983, when Michael Dickinson was responsible for all of the first five horses to finish – Bregawn, Captain John, Wayward Lad, Silver Buck and Ashley House. The 1986 winner, Dawn Run, is the only horse to have ever won both this race and the leading hurdle event, the Champion Hurdle. One of the most popular horses to win the Gold Cup was Desert Orchid, a grey who won the event in 1989. The following year's running was won by Norton's Coin, whose starting price of 100/1 represents the race's longest ever winning price.

The entire Cheltenham Festival was cancelled in 2001 because of an outbreak of foot-and-mouth disease. A replacement for the Cheltenham Gold Cup, the Gold Trophy Chase, was contested at Sandown in late April, but the Racing Post stated that this "lacked any strength in depth and was no substitute for the Gold Cup".^[5] The next three runnings were all won by Best Mate, who is the most recent of the four horses to have won the race three or more times.

In 2009, Kauto Star became the first horse to regain the Gold Cup. He overcame his stablemate and conqueror in 2008, Denman, who had recovered from a heart condition to take his place in the race.^[6] Timeform spokesperson Kieran Packman said of Kauto Star's performance, "it is the best Gold Cup-winning figure since the Arkle era in the mid-1960s".^[7]

One of the cups, a different one being awarded each year, was reported stolen on 14 July 2010 after a burglary at a home in Wormington, Gloucestershire.^[8]

Cheltenham Racecourse announced in September 2018 that it had been reunited with the original Cheltenham Gold Cup trophy, dating back to 1924, and will present it to the winner of the 2019 race. First awarded to five-year-old Red Splash, owned by Major Humphrey Wyndham, trained by Fred Withington and ridden by Dick Rees, it will now be re-introduced as a perpetual trophy, presented to the winning connections of the 2019 race and in future years.^[9]

In 2020 the Cheltenham Festival, and the Gold Cup in particular, was blamed for accelerating the spread of Covid-19 in the UK, being one of the last major sporting events to take place before national lockdowns were imposed by the government. In 2021 the Gold Cup was contested behind closed doors, as the rest of the festival was, resulting in a muted atmosphere. In 2022 Rachael Blackmore became the first female jockey to ride to victory at the Gold Cup on A Plus Tard, who she had ridden to second place the previous year.^[10]