Duppas Hill has a long history of sport and recreation. It is said that jousting took place there in medieval times and the story goes that Lord William de Warenne was treacherously slain there during a joust in 1286.
Duppas Hill was the site of the Croydon workhouse. In 1726 the Vestry of Croydon resolved to erect the town's first workhouse at a site on what was then 'Dubber's Hill'. The establishment was open by the end of the following year and governed by a committee of Trustees. In 1836 it became the Croydon Poor Law Union workhouse. The workhouse moved to Thornton Heath in 1866 but the infirmary remained in the Duppas Hill buildings until 1885 and the founding of what became Mayday Hospital close to the new workhouse.
There has been a public park at Duppas Hill since 1865, when the Croydon Board of Health bought land from the Ecclesiastical Commissioners for £2,000 to create Croydon's first recreation ground. It was laid out with paths, a bandstand, pavilion and an ornate drinking fountain. The Board of Health had to deal with cattle trespassing, drinking booths and other problems. The Board had proposed enclosing it with iron posts and railings intending to turn the area into a park rather than a recreation ground for all to enjoy sports and games freely, and in particular aimed to restrict horse-riding. Some of the Board wanted to ban horse-riding completely on the public open space, others to ban grooms exercising horses but not the general public riding for pleasure. Sir Francis Head, a famous soldier who lived at Duppas Hall overlooking the park, chaired a large public meeting to prevent the enclosure, wrote letters and memoranda to the press and headed a memorial of 3,500 people protesting against enclosure. He argued that the horse riders protected defenceless ladies, but he was eventually satisfied with notices forbidding people from exercising their horses, with Duppas Hill becoming the space for recreation it still is today.
Today the park is still a recreation ground and cricket is still played there. Part of the site was used as the Heath Clark school, later part of Croydon College, which has now been developed into housing.