Town’s U18s have been drawn at home to Winslow United in round one of the FA Youth Cup.
The game against the side from the Spartan South Midlands League - step six - will take place on a date yet to be set at Portman Road before Saturday 6th November.
Last season, the team coached by Adem Atay reached the semi-finals of the competition before losing 2-1 to Liverpool in the semi-finals.
Town have won the Youth Cup on three occasions, in 1973, 1975 and in 2005.
The U18s are in behind-closed-doors Professional Development League Cup action against Peterborough at Playford Road on Saturday morning, a game which was postponed last week.
The Blues are in Group D along with Posh, Sheffield United and Coventry, who beat Town 6-2 at their training ground in Town's opening game in the competition.
Meanwhile, 18-year-old academy striker Yousuf Hoque trained with a 38-member preliminary Bangladesh squad yesterday ahead of their AFC U23 Asian Cup qualifiers in Kuwait in late October.
Coach Maruful Haque said recently that he will run the rule over the Blues second-year scholar during the sessions and will select him for the final squad if he impresses.