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.

With Football League reorganisation looming at the end of the season, Colchester's priority for the 1957–58 season was to finish in the top half of the table to join the top half of the Third Division North to form the new nationwide Third Division.

During the campaign, Benny Fenton's squad suffered from numerous call-ups for national service, and as such Fenton brought in reinforcements in November with Neil Langman arriving from Plymouth Argyle for £6,750 and John Evans for £4,000 from Liverpool.

Meanwhile, Birmingham City offered Colchester £10,000 for winger Peter Wright, but he opted to remain as a part-time player.

[18] Players making their first-team Colchester United debut in a fully competitive match.