| Season | Competition |
Round Reached | Date |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 2001/2002 | 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
| (Full Members) | Southern Section Quarter-Final | Tue 26 Nov | Chelsea | 2 - 2 | Ipswich Town |
| after extra time, 90 minutes 2-2, Chelsea won 4-3 on penalties |
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| 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 |
| (Full Members) | Southern Section Semi-Final | Wed 27 Feb | Norwich City | 2 - 0 | Ipswich Town |
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| 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 |
| (Full Members) | Southern Section Semi-Final | Tue 23 Jan | Ipswich Town | 2 - 3 | Chelsea |
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| 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 |
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| 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 |
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| 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 |
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| 1985/1986 | F.A. Cup | 4th Round 2nd Replay | Thu 06 Feb | Ipswich Town | 0 - 1 | West Ham Utd. |
| after extra time, 90 minutes 0-0 |
| League Cup | Quarter Final | Tue 21 Jan | Liverpool | 3 - 0 | Ipswich Town |
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| 1984/1985 | F.A. Cup | 6th Round Replay | Wed 13 Mar | Ipswich Town | 0 - 1 | Everton |
| League Cup | Semi Final | Wed 06 Mar | Norwich City | 2 - 0 | Ipswich Town |
| Norwich City won 2-1 on aggregate |
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| 1983/1984 | F.A. Cup | 4th Round | Sat 28 Jan | Shrewsbury Tn. | 2 - 0 | Ipswich Town |
| League Cup | 4th Round | Wed 30 Nov | Ipswich Town | 0 - 1 | Norwich City |
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| 1982/1983 | F.A. Cup | 5th Round | Sat 19 Feb | Norwich City | 1 - 0 | Ipswich Town |
| League Cup | 2nd Round | Tue 26 Oct | Liverpool | 2 - 0 | Ipswich Town |
| Liverpool won 4-1 on aggregate |
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| 1981/1982 | F.A. Cup | 5th Round | Sat 13 Feb | Shrewsbury Tn. | 2 - 1 | Ipswich Town |
| League Cup | Semi Final | Tue 09 Feb | Liverpool | 2 - 2 | Ipswich Town |
| Liverpool won 4-2 on aggregate |
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| 1980/1981 | F.A. Cup | Semi Final | Sat 11 Apr | Man. City | 1 - 0 | Ipswich Town |
| after extra time, 90 minutes 0-0; played at Villa Park |
| League Cup | 4th Round | Tue 28 Oct | Birmingham C. | 2 - 1 | Ipswich Town |
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| 1979/1980 | F.A. Cup | 6th Round | Sat 08 Mar | Everton | 2 - 1 | Ipswich Town |
| League Cup | 2nd Round | Tue 04 Sep | Coventry City | 0 - 0 | Ipswich Town |
| Coventry City won 1-0 on aggregate |
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| 1978/1979 | F.A. Cup | 6th Round | Sat 10 Mar | Ipswich Town | 0 - 1 | Liverpool |
| League Cup | 2nd Round | Wed 30 Aug | Blackpool | 2 - 0 | Ipswich Town |
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| 1977/1978 | F.A. Cup | Final | Sat 06 May | Ipswich Town | 1 - 0 | Arsenal |
| played at Wembley |
| League Cup | 4th Round | Tue 29 Nov | Ipswich Town | 1 - 2 | Man. City |
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| 1976/1977 | F.A. Cup | 4th Round Replay | Wed 02 Feb | Wolves | 1 - 0 | Ipswich Town |
| League Cup | 2nd Round Replay | Tue 07 Sep | Brighton & HA | 2 - 1 | Ipswich Town |
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| 1975/1976 | F.A. Cup | 4th Round Replay | Tue 27 Jan | Wolves | 1 - 0 | Ipswich Town |
| League Cup | 2nd Round | Tue 09 Sep | Leeds Utd. | 3 - 2 | Ipswich Town |
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| 1974/1975 | F.A. Cup | Semi Final Replay | Wed 09 Apr | West Ham Utd. | 2 - 1 | Ipswich Town |
| played at Stamford Bridge |
| League Cup | Quarter Final Replay | Tue 10 Dec | Ipswich Town | 1 - 2 | Norwich City |
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| 1973/1974 | F.A. Cup | 5th Round | Sat 16 Feb | Liverpool | 2 - 0 | Ipswich Town |
| League Cup | 4th Round | Wed 21 Nov | Ipswich Town | 1 - 3 | Birmingham C. |
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| 1972/1973 | F.A. Cup | 4th Round | Sat 03 Feb | Chelsea | 2 - 0 | Ipswich Town |
| League Cup | 3rd Round | Tue 03 Oct | Ipswich Town | 1 - 2 | Stoke City |
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| 1971/1972 | F.A. Cup | 4th Round | Sat 05 Feb | Birmingham C. | 1 - 0 | Ipswich Town |
| League Cup | 2nd Round | Tue 07 Sep | Ipswich Town | 1 - 3 | Man. Utd. |
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| 1970/1971 | F.A. Cup | 5th Round Replay | Tue 16 Feb | Ipswich Town | 0 - 1 | Stoke City |
| League Cup | 2nd Round Replay | Mon 28 Sep | Arsenal | 4 - 0 | Ipswich Town |
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| 1969/1970 | F.A. Cup | 3rd Round | Sat 03 Jan | Ipswich Town | 0 - 1 | Man. Utd. |
| League Cup | 3rd Round Replay | Tue 30 Sep | West Brom. | 2 - 0 | Ipswich Town |
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| 1968/1969 | F.A. Cup | 3rd Round | Sat 04 Jan | Everton | 2 - 1 | Ipswich Town |
| League Cup | 2nd Round | Tue 03 Sep | Ipswich Town | 2 - 4 | Norwich City |
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| 1967/1968 | F.A. Cup | 3rd Round | Sat 27 Jan | Chelsea | 3 - 0 | Ipswich Town |
| League Cup | 3rd Round | Wed 11 Oct | Stoke City | 2 - 1 | Ipswich Town |
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| 1966/1967 | F.A. Cup | 5th Round Replay | Tue 14 Mar | Ipswich Town | 0 - 3 | Man. City |
| League Cup | 3rd Round | Tue 04 Oct | Birmingham C. | 2 - 1 | Ipswich Town |
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| 1965/1966 | F.A. Cup | 3rd Round Replay | Tue 25 Jan | Ipswich Town | 2 - 3 | Southport |
| League Cup | Quarter Final | Wed 17 Nov | Cardiff City | 2 - 1 | Ipswich Town |
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| 1964/1965 | F.A. Cup | 4th Round | Sat 30 Jan | Tottenham H. | 5 - 0 | Ipswich Town |
| League Cup | 2nd Round | Wed 23 Sep | Coventry City | 4 - 1 | Ipswich Town |
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| 1963/1964 | F.A. Cup | 4th Round Replay | Wed 29 Jan | Stoke City | 1 - 0 | Ipswich Town |
| League Cup | 2nd Round Replay | Thu 03 Oct | Walsall | 1 - 0 | Ipswich Town |
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| 1962/1963 | F.A. Cup | 4th Round | Wed 30 Jan | Leicester City | 3 - 1 | Ipswich Town |
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| 1961/1962 | F.A. Cup | 4th Round Replay | Tue 30 Jan | Ipswich Town | 1 - 2 | Norwich City |
| League Cup | 4th Round | Mon 11 Dec | Blackburn R. | 4 - 1 | Ipswich Town |
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| 1960/1961 | F.A. Cup | 3rd Round | Sat 07 Jan | Southampton | 7 - 1 | Ipswich Town |
| League Cup | 1st Round | Tue 11 Oct | Ipswich Town | 0 - 2 | Barnsley |
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| 1959/1960 | F.A. Cup | 3rd Round | Sat 09 Jan | Ipswich Town | 2 - 3 | Peterborough |
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| 1958/1959 | F.A. Cup | 5th Round | Sat 14 Feb | Ipswich Town | 2 - 5 | Luton Town |
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| 1957/1958 | F.A. Cup | 4th Round | Sat 25 Jan | Man. Utd. | 2 - 0 | Ipswich Town |
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| 1956/1957 | F.A. Cup | 3rd Round | Sat 05 Jan | Ipswich Town | 2 - 3 | Fulham |
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| 1955/1956 | F.A. Cup | 1st Round | Sat 19 Nov | Peterborough | 3 - 1 | Ipswich Town |
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| 1954/1955 | F.A. Cup | 3rd Round Replay | Wed 12 Jan | Bishop Auck. | 3 - 0 | Ipswich Town |
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| 1953/1954 | F.A. Cup | 5th Round | Sat 20 Feb | Preston N.E. | 6 - 1 | Ipswich Town |
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| 1952/1953 | F.A. Cup | 3rd Round | Sat 10 Jan | Everton | 3 - 2 | Ipswich Town |
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| 1951/1952 | F.A. Cup | 3rd Round 2nd Replay | Mon 21 Jan | Ipswich Town | 1 - 2 | Gateshead |
| after extra time, 90 minutes ?-? |
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| 1950/1951 | F.A. Cup | 2nd Round | Sat 09 Dec | Brighton & HA | 2 - 0 | Ipswich Town |
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| 1949/1950 | F.A. Cup | 3rd Round | Sat 07 Jan | West Ham Utd. | 5 - 1 | Ipswich Town |
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| 1948/1949 | F.A. Cup | 1st Round | Sat 04 Dec | Ipswich Town | 0 - 3 | Aldershot |
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| 1947/1948 | F.A. Cup | 1st Round | Sat 29 Nov | Swindon Town | 4 - 2 | Ipswich Town |
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| 1946/1947 | F.A. Cup | 2nd Round Replay | Wed 18 Dec | Ipswich Town | 0 - 1 | Walsall |
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| 1945/1946 | F.A. Cup | 2nd Round | Sat 15 Dec | Ipswich Town | 0 - 2 | Q.P.R. |
| Queens Park Rangers won 6-0 on aggregate |
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| 1938/1939 | F.A. Cup | 3rd Round Replay | Wed 11 Jan | Ipswich Town | 1 - 2 | Aston Villa |
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| 1937/1938 | F.A. Cup | 1st Round | Sat 27 Nov | Yeovil Town | 2 - 1 | Ipswich Town |
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| 1936/1937 | F.A. Cup | 2nd Round | Sat 12 Dec | Ipswich Town | 1 - 2 | Spennymoor |
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