Town have drawn Manchester United away in the third round of the Capital One Cup.
The teams last met in the competition back in the 1997/98 season when goals from Alex Mathie and Mauricio Taricco saw the Blues to a 2-0 victory at Portman Road.
In 1971/72 they met at the second round stage at Portman Road, United winning 3-1 via goals from George Best (2) and Willie Morgan, Jimmy Robertson having put the Blues ahead.
Town last faced the Red Devils in the league back in the 2001/02 relegation season when United won 4-0 at Old Trafford and 1-0 at Portman Road when Ruud van Nistelrooy won and converted a contentious penalty just before half-time.
Overall, the Blues have won 19 games between the sides (17 in the league) and the Red Devils 28 (24), while nine have been draws.
Third round ties will be played in the week commencing September 21st with the match at Old Trafford likely to be on the Wednesday with United in league action at Southampton on the Sunday.