| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2012/2013 | F.A. Cup | 3rd Round | Sat 05 Jan | Aston Villa | 2 - 1 | Ipswich Town |
| League Cup | 2nd Round | Tue 28 Aug | Carlisle Utd. | 2 - 1 | Ipswich Town |
| after extra time, 90 minutes 1-1 |
| 2011/2012 | F.A. Cup | 3rd Round | Sat 07 Jan | Hull City | 3 - 1 | Ipswich Town |
| League Cup | 1st Round | Tue 09 Aug | Ipswich Town | 1 - 2 | Northampton |
| 2010/2011 | F.A. Cup | 3rd Round | Sun 09 Jan | Chelsea | 7 - 0 | Ipswich Town |
| League Cup | Semi Final | Tue 25 Jan | Arsenal | 3 - 0 | Ipswich Town |
| Arsenal won 3-1 on aggregate |
| 2009/2010 | F.A. Cup | 4th Round | Sat 23 Jan | Southampton | 2 - 1 | Ipswich Town |
| League Cup | 2nd Round | Tue 25 Aug | Peterborough | 2 - 1 | Ipswich Town |
| 2008/2009 | F.A. Cup | 4th Round | Sat 24 Jan | Chelsea | 3 - 1 | Ipswich Town |
| League Cup | 3rd Round | Wed 24 Sep | Ipswich Town | 1 - 4 | Wigan Ath. |
| 2007/2008 | F.A. Cup | 3rd Round | Sat 05 Jan | Ipswich Town | 0 - 1 | Portsmouth |
| League Cup | 1st Round | Tue 14 Aug | Milton Keynes | 3 - 3 | Ipswich Town |
| after extra time, 90 minutes 2-2, Milton Keynes Dons won 5-3 on penalties |
| 2006/2007 | F.A. Cup | 5th Round | Sat 17 Feb | Watford | 1 - 0 | Ipswich Town |
| League Cup | 1st Round | Tue 22 Aug | Peterborough | 2 - 2 | Ipswich Town |
| after extra time, 90 minutes 1-1, Peterboro win 4-2 on pens |
| 2005/2006 | F.A. Cup | 3rd Round | Sat 07 Jan | Ipswich Town | 0 - 1 | Portsmouth |
| League Cup | 1st Round | Tue 23 Aug | Ipswich Town | 0 - 2 | Yeovil Town |
| 2004/2005 | F.A. Cup | 3rd Round | Sat 08 Jan | Ipswich Town | 1 - 3 | Bolton Wdrs. |
| League Cup | 2nd Round | Tue 21 Sep | Doncaster Rvs. | 2 - 0 | Ipswich Town |
| 2003/2004 | F.A. Cup | 4th Round | Sat 24 Jan | Ipswich Town | 1 - 2 | Sunderland |
| League Cup | 2nd Round | Tue 23 Sep | Notts. County | 2 - 1 | Ipswich Town |
| 2002/2003 | UEFA Cup | 2nd Round | Thu 14 Nov | Slovan Liberec | 1 - 0 | Ipswich Town |
| after extra time, 90 minutes 1-0, aggregate 1-1, Slovan Liberec won 4-2 on penalties |
| F.A. Cup | 4th Round | Sat 25 Jan | Sheff. Utd. | 4 - 3 | Ipswich Town |
| League Cup | 4th Round | Wed 04 Dec | Liverpool | 1 - 1 | Ipswich Town |
| after extra time, 90 minutes 1-1, Liverpool won 5-4 on penalties |
| 2001/2002 | UEFA Cup | 3rd Round | Thu 06 Dec | Inter Milan | 4 - 1 | Ipswich Town |
| Inter Milan won 4-2 on aggregate |
| F.A. Cup | 4th Round | Sun 27 Jan | Ipswich Town | 1 - 4 | Man. City |
| League Cup | 4th Round | Tue 27 Nov | Newcastle Utd. | 4 - 1 | Ipswich Town |
| 2000/2001 | F.A. Cup | 4th Round | Sat 27 Jan | Sunderland | 1 - 0 | Ipswich Town |
| League Cup | Semi Final | Wed 31 Jan | Birmingham C. | 4 - 1 | Ipswich Town |
| after extra time, 90 minutes 2-1, Birmingham City won 4-2 on aggregate |
| 1999/2000 | F.A. Cup | 3rd Round | Mon 13 Dec | Ipswich Town | 0 - 1 | Southampton |
| League Cup | 2nd Round | Tue 21 Sep | Ipswich Town | 1 - 1 | Crewe Alex. |
| Crewe Alexandra won 3-2 on aggregate |
| 1998/1999 | F.A. Cup | 4th Round | Sat 23 Jan | Everton | 1 - 0 | Ipswich Town |
| League Cup | 2nd Round | Tue 22 Sep | Luton Town | 4 - 2 | Ipswich Town |
| after extra time, 90 minutes 2-1, Luton Town won 5-4 on aggregate |
| 1997/1998 | F.A. Cup | 4th Round Replay | Tue 03 Feb | Sheff. Utd. | 1 - 0 | Ipswich Town |
| League Cup | Quarter Final | Wed 07 Jan | Ipswich Town | 2 - 2 | Chelsea |
| after extra time, 90 minutes 2-2, Chelsea won 4-1 on penalties |
| 1996/1997 | F.A. Cup | 3rd Round | Sat 04 Jan | Nottm. Forest | 3 - 0 | Ipswich Town |
| League Cup | Quarter Final | Tue 21 Jan | Ipswich Town | 0 - 1 | Leicester City |
| 1995/1996 | F.A. Cup | 5th Round | Sat 17 Feb | Ipswich Town | 1 - 3 | Aston Villa |
| League Cup | 2nd Round | Tue 03 Oct | Ipswich Town | 1 - 2 | Stockport Co. |
| after extra time, 90 minutes 1-1, Stockport County won 3-2 on aggregate |
| 1994/1995 | F.A. Cup | 3rd Round | Sat 07 Jan | Wrexham | 2 - 1 | Ipswich Town |
| League Cup | 2nd Round | Wed 05 Oct | Bolton Wdrs. | 1 - 0 | Ipswich Town |
| Bolton Wanderers won 4-0 on aggregate |
| 1993/1994 | F.A. Cup | 5th Round Replay | Wed 02 Mar | Ipswich Town | 1 - 2 | Wolves |
| League Cup | 3rd Round | Wed 27 Oct | Liverpool | 3 - 2 | Ipswich Town |
| 1992/1993 | F.A. Cup | 6th Round | Sat 06 Mar | Ipswich Town | 2 - 4 | Arsenal |
| League Cup | Quarter Final Replay | Wed 03 Feb | Sheff. Wed. | 1 - 0 | Ipswich Town |
| 1991/1992 | F.A. Cup | 5th Round Replay | Wed 26 Feb | Liverpool | 3 - 2 | Ipswich Town |
| after extra time, 90 minutes ?-? |
| League Cup | 2nd Round | Tue 08 Oct | Ipswich Town | 0 - 2 | Derby County |
| Derby County won 2-0 on aggregate |
| 1990/1991 | F.A. Cup | 3rd Round | Sat 05 Jan | Southampton | 3 - 2 | Ipswich Town |
| League Cup | 3rd Round | Tue 30 Oct | Ipswich Town | 0 - 2 | Southampton |
| 1989/1990 | F.A. Cup | 4th Round | Sat 27 Jan | Barnsley | 2 - 0 | Ipswich Town |
| League Cup | 2nd Round | Tue 03 Oct | Tranmere Rvs. | 1 - 0 | Ipswich Town |
| Tranmere Rovers won 2-0 on aggregate |
| 1988/1989 | F.A. Cup | 3rd Round | Sat 07 Jan | Nottm. Forest | 3 - 0 | Ipswich Town |
| League Cup | 4th Round | Wed 30 Nov | Aston Villa | 6 - 2 | Ipswich Town |
| 1987/1988 | F.A. Cup | 3rd Round | Sun 10 Jan | Ipswich Town | 1 - 2 | Man. Utd. |
| League Cup | 4th Round | Tue 17 Nov | Ipswich Town | 0 - 1 | Luton Town |
| 1986/1987 | F.A. Cup | 3rd Round | Sat 10 Jan | Ipswich Town | 0 - 1 | Birmingham C. |
| League Cup | 3rd Round | Tue 28 Oct | Cambridge U. | 1 - 0 | Ipswich Town |
