The Hastings & St Leonards Football Association was founded in 1892 and quickly established a competition for local clubs known as the Carlisle Cup. In 1902, a second competition—the Hillier Cup—was introduced, followed by the Brassey Cup in 1905.
By 1920, the association was overseeing seven competitions for teams of varying standards from across the area. In 1921, the Hastings F.A. reorganised these competitions into a formal three‑division league system with promotion and relegation, creating the Hastings League. Under this new structure, the Carlisle Cup became Division One, the Hillier Cup formed Division Two, and the Old Boys Cup was designated as Division Three, with each divisional champion continuing to receive the original named trophies.
By 1951, the league had expanded to four divisions, including an East and West split for Division Three, as well as a youth section. Over time, it might have been expected that the league would gradually lose clubs to the East Sussex League, which had been adding divisions of its own. By 1971, the Hastings League merged with the Eastbourne League to form the Eastbourne & Hastings League.
Sources: British Newspaper Archive.