The Hastings & St Leonards Football Association was founded in 1892 and quickly set up a competition for local clubs to compete in named the 'Carlisle Cup'. In 1902 an additional competition was set up named the 'Hillier Cup' and then the 'Brassey Cup' was also founded in 1905
By 1920 the association was running seven competitons for teams around the area of varying standards. In 1921 the Hastings F.A. decided to turn the competitions into a formal three league system with relegation and promotion and the Hastings League was set up. The Carlisle Cup became Division One, Hillier Cup became Division Two and the Old Boys Cup the new Division Three, with the champions of each division winning the old named trophies.
By 1951 the league was running four divisions, including a split east and west Division Three, plus a youth section. One would assume the league would lose teams to the East Sussex League over the years, who introduced additional divisions and by 1979 the Hastings League merged with the Eastbourne League to form the Eastbourne and Hastings League.