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.

Manager Benny Fenton assembled his own squad for the 1955–56 season, bringing in goalkeeper Percy Ames from Tottenham Hotspur, while also signing a number of players from Scottish junior football including John Fowler, Bobby Hill and Sammy McLeod.

Fenton's side played an exciting attacking game. They scored 76 goals in the league, with Kevin McCurley scoring a club Football League best total of 29 goals, and strike partner Ken Plant scoring 17. Both players notched two hat-tricks each during the season as the club safely finished the campaign in 12th-place.

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