After winning the Brighton, Hove & District League, Haywards Heath moved up to the Sussex County League. After top four finishes in four of their first five seasons in league, they finished bottom of the league in 1932–33. In 1941–42 the club won the Sussex Senior Cup. After World War II they were placed in the Eastern Division of the league for the 1945–46 season, going on to win the division. The following season saw the league revert to a single division, with the club winning back-to-back titles in 1949–50 and 1950–51.