The 1957–58 season was Colchester United's 16th season in their history and their eighth 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. They were eliminated at the first round stage of the cup for the fifth successive season, on this occasion to non-league side Wisbech Town. In the league, with the division being restructured at the end of the season, Colchester managed to finish in the top half of the table by three points to avoid a move to the newly formed Fourth Division, instead remaining in the third tier.