The East Sussex League was founded as the East Sussex Senior League in 1896 at a meeting held at the Royal Oak in Lewes on 15 May. Before this, the strongest teams in the county met only in cup ties or friendly matches; the creation of a senior league provided a structured competition in which clubs of similar standard could play regularly. The league champions would then face the winners of the West Sussex League—also formed in 1896—in the Irish Rifles’ Cup (now the RUR Cup) to decide the overall champions of Sussex.
A junior division was introduced for the 1898–99 season, consisting largely of reserve sides from senior-division clubs, but it lasted only three years. Membership remained stable during the league’s first decade, but numbers declined after the 1906–07 season, leading to a three-year period of inactivity. Even after reforming, the league struggled to expand, in contrast to the West and Mid Sussex leagues, which were attracting new clubs and developing additional divisions. It was not until 1920 that the East Sussex Senior League began to sustain consistently healthy membership numbers.
By the 1920s, all member clubs were based around Hastings and Eastbourne, while teams from further west tended to play in the Mid Sussex, Brighton, or Lewes leagues. Membership grew gradually through the 1930s until the outbreak of the Second World War in 1939. During the war the league operated Eastern and Western sections; Hastings Rangers beat Heathfield United 9–1 in a play-off held at Wadhurst to determine the wartime champions.
The league was re-formed in 1946, and membership remained steady. Rye United, Hollington United, and Hastings Rangers were particularly dominant in intermediate football during this era. However, the introduction of Division Two in the Sussex County League drew stronger clubs away from the ESFL. Although the East Sussex league continued to operate a single division at a time when comparable competitions were expanding, it struggled to keep pace. In the 1950s the league chairman even proposed merging with the Hastings League, which had a broader catchment area extending into Kent. The merger did not proceed.
Instead, the East Sussex League increased its membership independently, adding a second division ahead of the 1959–60 season. It expanded further in the 1960s, eventually running five divisions and welcoming clubs from Tunbridge Wells, Tenterden, and Hawkhurst. Membership remained stable throughout the 1970s and 1980s, and the league grew again after absorbing Hastings-area clubs following the breakup of the Eastbourne & Hastings League in 1988.
The 1990s saw clubs such as Shinewater Association and Seaford win the Premier Division and progress to county football, though overall membership began to decline slowly. The collapse of the Eastbourne League in 2009 helped boost numbers, prompting the creation of another division. As of 2021, the East Sussex League comprises six divisions headed by the Premier Division. Several clubs remain based along the Sussex–Kent border, which has led to the competition being known in the past as the East Sussex Border League. However, some of its stronger sides, including the first teams of Hollington United and Sidley United, have since moved to the Mid Sussex League in search of a higher playing standard.
Sources: East Sussex Football League, British Newspaper Archive, Skraffstat, Aaron Hill.