The club won their first trophy in the 1886–87 season, triumphing 2–1 against a team representing Ipswich School in the final of the Suffolk Challenge Cup. In 1888 the club merged with Ipswich Rugby Club to form Ipswich Town F.C. In 1890, the club entered the qualifying rounds of the FA Cup for the first time and was knocked out in the final qualifying round by the 93rd Highlanders. The club experienced scant success in the Cup during the 1890s but won a number of local cup competitions, including the Suffolk Senior Cup and the Ipswich Charity Cup. Having received invitations to join from both the Southern League and the Norfolk & Suffolk League, Ipswich joined the latter in the 1899–1900 season, finishing fourth in their first league season. They were league runners-up in 1902–03. In 1903 they also entered a team into the new South East Anglian League and were its inaugural champions. They left the South East Anglian League in 1906, but continued playing in the Norfolk & Suffolk League.