The 1955–56 season was Colchester United's 14th season in their history and their sixth season in the Third Division South, the third tier of English football. Alongside competing in the Third Division South, the club also participated in the FA Cup in which the club were eliminated by Torquay United in the first round. The season was Benny Fenton's first full campaign in charge, and after building his own squad over the summer, he led Colchester to their highest position since the 1951–52 season with a 12th-placed finish. This came on the back of two consecutive seasons of successful re-election applications.