Town have drawn Premier League new boys Fulham at home in the second round of the Carabao Cup and will face Rochdale or Sheffield Wednesday in the third, also at Portman Road, if they win that tie.
Second round ties will be played on either the 15th or 16th September with the third round taking place on 22nd and 23rd September.
The Blues and the Cottagers last met in the League Cup in the 1996/97 season when the first leg at Craven Cottage ended 1-1 with the locally-born Simon Milton netting a stunner for Town.
At Portman Road, the Blues ran out 4-2 victors with Alex Mathie scoring twice and Danny Sonner and Steve Sedgley (pen), who also conceded an own goal, once each.
The teams also faced one another in the competition in 1973/74 when the initial tie in London ended 2-2 - Trevor Whymark and Clive Woods the Town scorers - and the replay at Portman Road 2-1 to Bobby Robson's side with Colin Harper and Colin Viljoen on target.
The clubs last faced one another in the Championship when the Blues were beaten 2-0 at home - Neeskens Kebano and Rui Fonte the scorers - and 4-1 away after Joe Garner had given Town the lead, Jordan Spence having been red-carded in the 54th minute. Ryan Sessegnon and Aboubakar Kamara each hit a brace for the Whites who went on to win promotion via the play-offs.
Drawing Fulham at home means the Blues start the season with four games at home, something which hasn't happened since the 1923/24 season in the Southern Amateur League.
If Town beat Fulham and Rochdale defeat Sheffield Wednesday in their second round tie, then the Blues will face Dale twice at home in a few days with the League One game at Portman Road scheduled for Saturday 26th September.