Not to be confused with the village of the same name in Cheshire, Prestbury in Gloucestershire is a residential suburb on the northern outskirts of Cheltenham, in the foothills of Cotswolds. Prestbury Park is known to have existed as long ago as 1136, when it was created by the Bishop of Hereford, and was subsequently used as a medieval deer park and later, in the eighteenth and nineteenth centuries, as farmland. The Prestbury Park site was employed, temporarily, as a horse racing venue from 1831 onwards, but it was not until the turn of the twentieth century that it became synonymous with Cheltenham Racecourse.

In 1881, Prestbury Park was bought by William Baring Bingham, who initially used it as his stud farm, before consenting to ‘lend’ the land for the revival of steeplechasing, under National Hunt Rules, in 1898. Four years later, Cheltenham Racecourse staged a forerunner of what would become the National Hunt, or Cheltenham, Festival and the rest, as they say, is history. Nowadays, Prestbury Park is home to three courses, namely the original ‘Old’ Course, the ‘New’ Course, which was used for the first time in 1967, and the idiosyncratic Cross Country Course, which was added in 1995.

The Cathcart Challenge Cup was a steeplechase staged, in various guises, at the Cheltenham Festival between 1938 and 2004 but, for most of its existence, was a Grade Two event, run over 2 miles 5 furlongs, on the New Course at Prestbury Park. The Cathcart Challenge Cup was named in honour of Frederick Cathcart, Chairman of the Steeplechase Company (Cheltenham) Limited, incorporated in 1907, Clerk of the Course at Prestbury Park and a hugely influential figure in the evolution of the Cheltenham Festival.

Bizarrely, between 1975 and 1977, the Cathcart Challenge Cup in its traditional form was replaced by the Cathcart Champion Hunters’ Chase, run over 3 miles 1 furlong. Nevertheless, in its original incarnation, the Cathcart Challenge Cup was typically contested by ‘intermediate’ steeplechasers or, in other words, those who lacked the speed for the Queen Mother Champion Chase and the stamina for the Cheltenham Gold Cup. The last winner of the Cathcart Challenge Cup was Our Armageddon, trained by Richard Guest, in 2004 and the following year the race was replaced by a similar event, the Festival Trophy – now better known as the Ryanair Chase – when the Cheltenham Festival was extended to four days for the first time.

The Cheltenham Gold Cup is the most prestigious steeplechase in Europe and has been run, in its current guise, at the Cheltenham Festival, in mid-March, most years since 1924. Indeed, in the better part of a century since the inaugural running, the Cheltenham Gold Cup has been out-and-out abandoned just five times in its history.

The Cheltenham Festival was cancelled, in its entirety, in 1943 and 1944, when Cheltenham Racecourse was used as a military training facility during World War II, and again in 2001, when the fixture was initially postponed until April, but called off completely when the racecourse subsequently fell within a foot-and-mouth exclusion zone. In 1931, the Cheltenham Gold Cup fell victim to a bitterly cold March and it was a similar story in 1937, when a mild, but very wet, winter heralded another cold, wintry March, with frequent snowfall.

Snow, once again, threatened to intervene in 1940, but the Cheltenham Gold Cup was not abandoned, but rather rescheduled six days later. The 1978 renewal was also postponed because of snow and, for the first time since its inception, the Cheltenham Gold Cup was run in April instead of March. Since then, the only day of the Cheltenham Festival lost to bad weather was the second day in 2008, which was cancelled due to high winds; the races due to be run on that day were rescheduled for the Thursday and Friday and the running of the Cheltenham Gold Cup was unaffected.

The Cheltenham Gold Cup, run over 3 miles, 2 furlongs and 70 yards, and 22 notoriously stiff fences, at Prestbury Park in Gloucestershire, is the highlight of the Cheltenham Festival, staged annually in March. The race was first staged, in its current guise, in 1924 and, while it is not the most valuable steeplechase run in Britain – that distinction belongs, by a fair margin, to the Grand National – it is, in fact, the most valuable conditions, or non-handicap, steeplechase. In 2019, total prize money for the Cheltenham Gold Cup was £625,000, with the winner receiving £351,688.

The Gold Cup, run over 2 miles, 3 furlongs and 210 yards, and no obstacles at all, at Ascot Racecourse in Berkshire, is similarly the highlight of Royal Ascot week, staged annually in June. The Gold Cup is, far and away, the older of the two races, having been staged for the first time, in the presence of King George III – he of ‘madness’ fame – in 1807. Nowadays, the race is the most prestigious event in Britain and, arguably, in the world, for horses that specialise in racing over long distances, otherwise known as ‘stayers’. Prestigious though it may be, in 2018, total prize money for the Gold Cup was ‘just’ £500,000, with the winning receiving £283,550; when compared with the Cheltenham Gold Cup, the Gold Cup is actually one race that gives lie to the often-repeated claim that National Hunt racing is the ‘poor relation’ of Flat racing.