For more than 480 years the turf arena, which lies immediately west of the red stone walls, has related to sport, and even before that its played its part in the lives of the citizens as the scene of sport and more serious pageantry.
There is no more popular meeting in the North than Chester’s three-day May Festival meeting, and the Chester Cup Day is one set aside for a great influx of racegoers from all parts of the country. The story of the Roodee’s links can be traced back to 1539, when Henry VIII was on the throne and Henry Gee was the mayor of Chester. He promoted a horse race as part of the Shrovetide sports meeting. However the principal event prior to horseracing was an annual football match between the drapers and the shoemakers of the city in which the ancient cross on the Roodee served as one goal and Gee’s home as the other.
However the last fixture in 1533 caused that many injuries to both sets of players that it was banned by Gee and no future matches took place. In 1609, Robert Ambridge, the sheriff of Chester presented three silver bells later renamed the St George’s Bells, because the race was staged on St George’s Day, these were given to the first three horses past the judge, which incorporated five circuits of the Roodee. It would be fitting to be able to cite this St George’s Bells as the precursor of the Chester Cup race, but actually it was the forerunner of the City Plate, which came to an end with the passing of the Municipal Capital Reforms Act of 1835, which made it illegal for public money to be devoted to racing prizes.
The Chester Cup was originally the Tradesman Cup and the winner in which horses had to start at the castle gate was Doge of Venice, which was owned by Sir Thomas Stanley of Hooton Hall, as an owner he also won the Sir Watkin Silver Cup at Wrexham racecourse in 1837 with the mare Violet. The citizens of Chester were however anxious that their horse race meeting on the Roodee should be one of the main turf events in the country, and following the loss of the municipal financial support, they increased their subscriptions, which resulted in the Chester Cup becoming an important race in the racing calendar.
The first really famous racehorse to win the Chester Cup was the prolific winning mare Alice Hawthorn in 1842. Owned by John Plummer of Skipton, the very next day she was saddled in a handicap stakes race, which she won easily, and went on to achieve a third success at the course the day after in the Cheshire Stakes. Ridden by Bumby Heseltine that record of three wins in successive days at the May Festival still stands.
When Hawthorn gained her Chester Cup success, she was handicapped at six stone, but two years later she had to carry 9st 8lbs, that race was won by the Duke of Richmond’s three year old Red Deer, trained at Goodwood by John Kent and ridden by the diminutive jockey Kitchener, who weighed just 3st 4lbs. If Red Deer made history by being the first three year to win the Chester Cup, it was bettered by another three old in 1852 called Joe Miller trained by William Day, who was the first horse to complete the Chester Cup and Ascot Gold Cup in the same year.
Eleven years later Asteroid came to Chester as the winner of the Ascot Gold Cup and completed a double on the Roodee. As remarkable tales of the turf go they do not come any better that the amazing feats performed by Willonyx, who was bought as a yearling for £700gns, who won the Chester Cup in 1911, then the Ascot Gold Cup and the Ascot Stakes in the same year, and then going on to Newmarket to land the Cesarewitch and just for good measure landed the Jockey Club Cup a fortnight later. The last horse to win the Chester Cup and Ascot Gold Cup in the same year was the Ed Dunlop trained Trip To Paris in 2015.
One of the most popular winners of the Chester Cup was Hare Hill in 1915 as was Agreement in 1959, ridden by Harry Carr for The Queen – the only monarch to have won the race. There have been nine dual winners of the Chester Cup, but the former trainer Barry Hills remains the only trainer to have trained four winners of the race, they were Arapahos, Rainbow High (twice) and Daraahem. The record attendance on Chester Cup day was in 1946 when Retsel won the Chester Cup ridden by Clifford Egerton Richards, the younger brother of Sir Gordon Richards in front of a crowd of 103,993.
My late grandfather Harry Shone was there that day, and said that the atmosphere was incredible, he told me that everyone just wanted something to celebrate after six years of the second world war. However, he told me that one of the most popular winners of the Chester Cup that he watched at the Roodee was Dick Turpin who won the race in 1933 by a head under the legendary jockey Sir Gordon Richards.
One of the most important races of the May Festival is the Chester Vase, first run in 1907, it soon became a noted Epsom Derby trial, in the early days it was a race for three and four-year olds. In 1959 the race was changed to include three year olds only. Fidalgo won the race that year and was runner up to Parthia in the Epsom Derby, the winner had won the Dee stakes at Chester that year, and Fidalgo went on to win the Irish Derby. In recent years Troy (1979) Henbit (1980) and Shergar (1981), all competed the Chester Vase and Epsom Derby double. The most recent horse to complete the double was the Aiden O’Brien trained Ruler of the World in 2013.
The Chester Vase and the Deestakes are now well-established Epsom Derby trials and continue to attract some of the very best three-year olds. The Ormonde Stakes named after the unbeaten triple crown winner of 1886, was bred by his owner the Duke Of Westminster not far from the racecourse at Eaton Hall stud. The Eaton Hall Stud was established in 1762 by the first Duke Of Westminster when he registered his famous orange colours.
The first Duke had his colours carried to victory in the three Epsom Derby’s and six Epsom Oaks, he was also a fearless gambler who reputedly lost over £250,000 in his lifetime. Many racing historians regard Ormonde as the greatest flat racehorse of all time and his regular jockey Fred Archer said that he was the best he had ever sat on, testament itself from a man that had been crowned champion jockey 13 times and rode 2,748 winners. In the early days the Ormonde Stakes was then often selected as the first outing for Ascot Gold
Cup contenders. In 1949 Alycidon completed the Ascot and Ormonde double. Then in 1958 there came another change when the race was open to four year olds and upwards and in that year the race was won by The Queen with Doutelle, who beat Ballymoss, the winner of the St Leger and the Coronation Cup, the Eclipse stakes and the King George before 1958.
Of the post war introductions, the Cheshire Oaks appeared on the calendar for the very first time with a view to becoming a classic trial for the Epsom Oaks. The first winner was Requette, the race was a Group 3 contest from 1971-85, it was then dropped to a listed race in 1986. Then is 1989 the race was reduced to a mile and three furlongs, despite its introduction as an Epsom Oaks trial, the only horse to land the Cheshire and Epsom Oaks double was the Sir Henry Cecil trained Light Shift in 2007.
However all that changed last year with in the John Gosden trained Enable, who not only went on to win the Epsom Oaks, but added the Irish Oaks, Yorkshire Oaks, King George & Queen Elizabeth Stakes and the Prix de I‘Arc de Triomphe, clearly arguably the greatest filly ever to have won at the Roodee. Losing the group status has always been a bone of contention, after Enable won her second Prix de I ‘Arc de Triomphe to establish the filly as one of the best fillies of all time, she deserves to be listed in the same breath as Sun Chariot and Oh So Sharp, truly great fillies of the turf.
The very first race of the May Festival is the Lily Agnes stakes, the race is named after a brilliant racehorse who will always be remembered as the dam of the great unbeaten Ormonde. It is worth remembering that she was well bred in her own right being by the 1863 2000gns and Epsom Derby winner Macaroni, as a racehorse she won 21 races including the Doncaster Cup, Ebor handicap and Northumberland Plate. It is fitting that the race named after her is for two year olds, as she was unbeaten in all her six starts as a two-year-old. Her owner the Duke of Westminster doted on the mare and he is reported to be have been devastated when she died at his Eaton Hall stud at the grand old age of 28.