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.

The flamboyant grey Desert Orchid is best remembered for his career as a steeplechaser, during which he won the Cheltenham Gold Cup, in 1989, and the King George VI Chase four times, in 1986, 1988, 1989 and 1990. However, ‘Dessie’ also enjoyed a brilliant hurdling career and first caught public attention with his meteoric rise through the ranks in his novice season over the small obstacles in 1983/84.

In that season, Desert Orchid won six of his eight starts, including the Grade One Tolworth Hurdle at Sandown in January and the Grade Two Kingwell Hurdle at Wincanton in February. He made his debut at the Cheltenham Festival in the Champion Hurdle, for which, despite still being a novice, he was sent at just 7/1; he failed to make much of an impact, though, fading from the second-last flight of hurdles to finish down the field behind Dawn Run.

The 1984/85 season was more of a struggle for Desert Orchid and he won just once, in the Listed Oteley Hurdle, now the Contenders Hurdle, at Sandown in January. Nevertheless, he took his place in Champion Hurdle once again but, having chased the frenetic pace set by Northern Trial, weakened quickly as the field approached the top of the hill and was pulled up before three out in the race eventually won by See You Then. So, while Desert Orchid did twice contest the Champion Hurdle, he never did win it.

Michael William Dickinson took over the licence at Poplar House, Dunkeswick, near Harewood, West Yorkshire from his father, Tony, in 1980 and wasted little time in revolutionising National Hunt racing. In three of the four seasons that Dickinson Jnr. held a licence – 1981/82, 1982/83 and 1983/84 – he was Champion Trainer; on the first two occasions, he sent out 84 winners and 120 winners, at a strike rate of 45% and 46%, respectively, from a yard with just 55 stables.

Michael Dickinson first won the Cheltenham Gold Cup in 1982, when he saddled Silver Buck to beat stable companion Bregawn by two lengths, for a notable 1-2 in the ‘Blue Riband’. However, in 1983, Dickinson saddled Bregawn and Captain John – who had already filled the first two places in the Hennessy Gold Cup the previous November – to finish first and second in the Cheltenham Gold Cup and, remarkably, Wayward Lad, Silver Buck and Ashley House to fill the next three places, for a record-breaking 1-2-3-4-5 for the yard. So, strictly speaking, Michael Dickinson won the Cheltenham Gold Cup just twice, but his so-called ‘Famous Five’, will always be remembered as one of the greatest training feats of all time.

The inaugural Cheltenham Festival was staged, as a two-day affair, in 1911, under the auspices of W.A. Baring Bingham, who owned the land at Prestbury Park, and Frederick Cathcart, Clerk of the Course at Cheltenham Racecourse. Cathcart would go on to create the Cheltenham Gold Cup in 1924 and the Champion Hurdle in 1927, but even before the addition of those two races, in 1923, the Cheltenham Festival had been extended to a three-day meeting. Various races came and went over the years, but the Festival remained a three-day meeting until 2005, when it was extended to four days, with the addition of several new races, including the Ryanair Chase and the Glenfarclas Cross Country Chase.

The Cheltenham Festival continues to evolve and, nowadays, consists of 28 races, including twelve at Grade One level. One of the four main ‘championship’ races – namely the Champion Hurdle, Queen Mother Champion Chase, Stayers’ Hurdle and Cheltenham Gold Cup – is the feature race on each of the four days and is complemented by two, or three, other Grade One races each day, plus a selection of lesser Graded races, Listed races and competitive handicaps.