Football League Cup 2023/24, Second Round |
 | 29.08.2023 |  | Reading | – | Ipswich Town | | 2:2 (1:1),
pen. 1:3 |
| Reading |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Exeter City | – | Ipswich Town | | 1:1 (0:1),
pen. 4:2 |
| Exeter |
Football League Cup 2009/10, First Round |
| 11.08.2009 | | Shrewsbury Town | – | Ipswich Town | | 3:3 aet
(2:2, 3:3),
pen. 2:4 |
| Shrewsbury |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Milton Keynes Dons | – | Ipswich Town | | 3:3 aet
(2:1, 2:2),
pen. 5:3 |
| Milton Keynes |
Football League Cup 2006/07, First Round |
| 22.08.2006 | | Peterborough United | – | Ipswich Town | | 2:2 aet
(1:0, 1:1),
pen. 4:2 |
| Peterborough |
Football League Cup 2002/03, Fourth Round |
| 04.12.2002 | | Liverpool | – | Ipswich Town | | 1:1 aet
(0:1, 1:1),
pen. 5:4 |
| Liverpool |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Ipswich Town | – | Crewe Alexandra | | 1:1 (1:0) |
| Ipswich |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Exeter City | – | Ipswich Town | | 1:1 (0:1) |
| Exeter |
Football League Cup 1997/98, Fifth Round |
| 07.01.1998 | | Ipswich Town | – | Chelsea | | 2:2 aet
(1:2, 2:2),
pen. 1:4 |
| Ipswich |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Ipswich Town | – | Torquay United | | 1:1 (0:1) |
| Ipswich |
Football League Cup 1996/97, Second round |
| 17.09.1996 | | Fulham | – | Ipswich Town | | 1:1 (1:0) |
| London |
Football League Cup 1995/96, Second round |
| 19.09.1995 | | Stockport County | – | Ipswich Town | | 1:1 (1:1) |
| Stockport |
Football League Cup 1992/93, Fifth Round |
| 19.01.1993 | | Ipswich Town | – | Sheffield Wednesday | | 1:1 (0:0) |
| Ipswich |
Football League Cup 1992/93, Fourth Round |
| 02.12.1992 | | Aston Villa | – | Ipswich Town | | 2:2 (0:0) |
| Birmingham |
Football League Cup 1992/93, Second round |
| 22.09.1992 | | Wigan Athletic | – | Ipswich Town | | 2:2 (0:1) |
| Wigan |
Football League Cup 1991/92, Second round |
| 25.09.1991 | | Derby County | – | Ipswich Town | | 0:0 |
| Derby |
Football League Cup 1990/91, Second round |
| 25.09.1990 | | Shrewsbury Town | – | Ipswich Town | | 1:1 |
| Shrewsbury |
Football League Cup 1987/88, Second round |
| 22.09.1987 | | Ipswich Town | – | Northampton Town | | 1:1 |
| Ipswich |
Football League Cup 1984/85, Fifth Round |
| 23.01.1985 | | Ipswich Town | – | Queens Park Rangers | | 0:0 |
| |
Football League Cup 1984/85, Third round |
| 30.10.1984 | | Ipswich Town | – | Newcastle United | | 1:1 |
| |
Football League Cup 1984/85, Second round |
| 10.10.1984 | | Derby County | – | Ipswich Town | | 1:1 |
| |
Football League Cup 1981/82, Semifinals |
| 09.02.1982 | | Liverpool | – | Ipswich Town | | 2:2 |
| Liverpool |
Football League Cup 1981/82, Third round |
| 10.11.1981 | | Ipswich Town | – | Bradford City | | 1:1 |
| |
Football League Cup 1980/81, Third round |
| 23.09.1980 | | Ipswich Town | – | Norwich City | | 1:1 |
| |
Football League Cup 1979/80, Second round |
| 04.09.1979 | | Coventry City | – | Ipswich Town | | 0:0 |
| |
Football League Cup 1976/77, Second round |
| 31.08.1976 | | Ipswich Town | – | Brighton & Hove Albion | | 0:0 |
| |
Football League Cup 1974/75, Fifth Round |
| 04.12.1974 | | Norwich City | – | Ipswich Town | | 1:1 |
| |
Football League Cup 1973/74, Third round |
| 31.10.1973 | | Fulham | – | Ipswich Town | | 2:2 |
| |
Football League Cup 1970/71, Second round |
| 08.09.1970 | | Ipswich Town | – | Arsenal | | 0:0 |
| |
Football League Cup 1969/70, Third round |
| 24.09.1969 | | Ipswich Town | – | West Bromwich Albion | | 1:1 |
| |
Football League Cup 1965/66, Third round |
| 13.10.1965 | | Workington | – | Ipswich Town | | 1:1 |
| |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | Ipswich Town | – | Walsall | | 0:0 |
| |
Football League Cup 1961/62, Second round |
| 03.10.1961 |  | Swansea Town | – | Ipswich Town | | 3:3 |
| |
