Football League Cup 2023/24, Fourth Round |
 | 01.11.2023 |  | Ipswich Town | – | Fulham | | 1:3 (0:1) |
| Ipswich |
Football League Cup 2022/23, First Round |
| 09.08.2022 | | Ipswich Town | – | Colchester United | | 0:1 (0:1) |
| Ipswich |
Football League Cup 2021/22, First Round |
| 10.08.2021 | | Ipswich Town | – | Newport County |  | 0:1 (0:1) |
| Ipswich |
Football League Cup 2020/21, Second round |
| 16.09.2020 | | Ipswich Town | – | Fulham | | 0:1 (0:1) * |
| Ipswich |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Luton Town | – | Ipswich Town | | 3:1 (2:0) |
| Luton |
Football League Cup 2017/18, Second round |
| 22.08.2017 | | Crystal Palace | – | Ipswich Town | | 2:1 (0:0) |
| London |
Football League Cup 2016/17, First Round |
| 09.08.2016 | | Ipswich Town | – | Stevenage | | 0:1 (0:0) |
| Ipswich |
Football League Cup 2015/16, Third round |
| 23.09.2015 | | Manchester United | – | Ipswich Town | | 3:0 (1:0) |
| Manchester |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Crawley Town | – | Ipswich Town | | 1:0 aet
(0:0) |
| Crawley |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Stevenage | – | Ipswich Town | | 2:0 (0:0) |
| Stevenage |
Football League Cup 2012/13, Second round |
| 28.08.2012 | | Carlisle United | – | Ipswich Town | | 2:1 aet
(0:1, 1:1) |
| Carlisle |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Ipswich Town | – | Northampton Town | | 1:2 (1:1) |
| Ipswich |
Football League Cup 2010/11, Semifinals |
| 25.01.2011 | | Arsenal | – | Ipswich Town | | 3:0 (0:0) |
| London |
Football League Cup 2009/10, Second round |
| 25.08.2009 | | Peterborough United | – | Ipswich Town | | 2:1 (1:1) |
| Peterborough |
Football League Cup 2008/09, Third round |
| 24.09.2008 | | Ipswich Town | – | Wigan Athletic | | 1:4 (0:0) |
| Ipswich |
Football League Cup 2005/06, First Round |
| 23.08.2005 | | Ipswich Town | – | Yeovil Town | | 0:2 (0:1) |
| Ipswich |
Football League Cup 2004/05, Second round |
| 21.09.2004 | | Doncaster Rovers | – | Ipswich Town | | 2:0 (1:0) |
| Doncaster |
Football League Cup 2003/04, Second round |
| 23.09.2003 | | Notts County | – | Ipswich Town | | 2:1 (2:1) |
| Nottingham |
Football League Cup 2001/02, Fourth Round |
| 27.11.2001 | | Newcastle United | – | Ipswich Town | | 4:1 (4:0) |
| Newcastle upon Tyne |
Football League Cup 2000/01, Semifinals |
| 31.01.2001 | | Birmingham City | – | Ipswich Town | | 4:1 aet
(1:0, 1:1) |
| Birmingham |
Football League Cup 2000/01, Second round |
| 19.09.2000 | | Millwall | – | Ipswich Town | | 2:0 (1:0) |
| London |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Crewe Alexandra | – | Ipswich Town | | 2:1 (0:1) |
| Crewe |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Luton Town | – | Ipswich Town | | 4:2 aet
(0:1, 2:1) |
| Luton |
Football League Cup 1996/97, Fifth Round |
| 21.01.1997 | | Ipswich Town | – | Leicester City | | 0:1 (0:1) |
| Ipswich |
Football League Cup 1995/96, Second round |
| 03.10.1995 | | Ipswich Town | – | Stockport County | | 1:2 aet
(1:0, 1:1) |
| Ipswich |
Football League Cup 1994/95, Second round |
| 05.10.1994 | | Bolton Wanderers | – | Ipswich Town | | 1:0 (0:0) |
| Bolton |
Football League Cup 1994/95, Second round |
| 21.09.1994 | | Ipswich Town | – | Bolton Wanderers | | 0:3 (0:1) |
| Ipswich |
Football League Cup 1993/94, Third round |
| 27.10.1993 | | Liverpool | – | Ipswich Town | | 3:2 (2:1) |
| Liverpool |
Football League Cup 1992/93, Fifth Round |
| 03.02.1993 | | Sheffield Wednesday | – | Ipswich Town | | 1:0 (0:0) * |
| Sheffield |
Football League Cup 1991/92, Second round |
| 08.10.1991 | | Ipswich Town | – | Derby County | | 0:2 (0:2) |
| Ipswich |
Football League Cup 1990/91, Third round |
| 30.10.1990 | | Ipswich Town | – | Southampton | | 0:2 |
| Ipswich |
Football League Cup 1989/90, Second round |
| 03.10.1989 | | Tranmere Rovers | – | Ipswich Town | | 1:0 |
| Birkenhead |
Football League Cup 1989/90, Second round |
| 19.09.1989 | | Ipswich Town | – | Tranmere Rovers | | 0:1 |
| Ipswich |
Football League Cup 1988/89, Fourth Round |
| 30.11.1988 | | Aston Villa | – | Ipswich Town | | 6:2 (2:0) |
| Birmingham |
Football League Cup 1988/89, Second round |
| 26.09.1988 | | Port Vale | – | Ipswich Town | | 1:0 |
| Stoke-on-Trent |
Football League Cup 1987/88, Fourth Round |
| 17.11.1987 | | Ipswich Town | – | Luton Town | | 0:1 |
| Ipswich |
Football League Cup 1986/87, Third round |
| 28.10.1986 | | Cambridge United | – | Ipswich Town | | 1:0 |
| Cambridge |
Football League Cup 1985/86, Fifth Round |
| 21.01.1986 | | Liverpool | – | Ipswich Town | | 3:0 |
| Liverpool |
Football League Cup 1984/85, Semifinals |
| 06.03.1985 | | Norwich City | – | Ipswich Town | | 2:0 |
| Norwich |
Football League Cup 1983/84, Fourth Round |
| 30.11.1983 | | Ipswich Town | – | Norwich City | | 0:1 |
| |
Football League Cup 1982/83, Second round |
| 26.10.1982 | | Liverpool | – | Ipswich Town | | 2:0 |
| Liverpool |
Football League Cup 1982/83, Second round |
| 05.10.1982 | | Ipswich Town | – | Liverpool | | 1:2 |
| Ipswich |
Football League Cup 1981/82, Semifinals |
| 02.02.1982 | | Ipswich Town | – | Liverpool | | 0:2 |
| |
Football League Cup 1980/81, Fourth Round |
| 28.10.1980 | | Birmingham City | – | Ipswich Town | | 2:1 |
| |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Middlesbrough | – | Ipswich Town | | 3:1 |
| |
Football League Cup 1979/80, Second round |
| 29.08.1979 | | Ipswich Town | – | Coventry City | | 0:1 |
| |
Football League Cup 1978/79, Second round |
| 30.08.1978 | | Blackpool | – | Ipswich Town | | 2:0 |
| |
Football League Cup 1977/78, Fourth Round |
| 29.11.1977 | | Ipswich Town | – | Manchester City | | 1:2 |
| |
Football League Cup 1976/77, Second round |
| 07.09.1976 | | Brighton & Hove Albion | – | Ipswich Town | | 2:1 * |
| |
Football League Cup 1975/76, Second round |
| 09.09.1975 | | Leeds United | – | Ipswich Town | | 3:2 |
| |
Football League Cup 1974/75, Fifth Round |
| 10.12.1974 | | Ipswich Town | – | Norwich City | | 1:2 * |
| |
Football League Cup 1973/74, Fourth Round |
| 21.11.1973 | | Ipswich Town | – | Birmingham City | | 1:3 |
| |
Football League Cup 1972/73, Third round |
| 03.10.1972 | | Ipswich Town | – | Stoke City | | 1:2 |
| |
Football League Cup 1971/72, Second round |
| 07.09.1971 | | Ipswich Town | – | Manchester United | | 1:3 |
| |
Football League Cup 1970/71, Second round |
| 28.09.1970 | | Arsenal | – | Ipswich Town | | 4:0 * |
| London |
Football League Cup 1969/70, Third round |
| 30.09.1969 | | West Bromwich Albion | – | Ipswich Town | | 2:0 * |
| West Bromwich |
Football League Cup 1968/69, Second round |
| 03.09.1968 | | Ipswich Town | – | Norwich City | | 2:4 |
| |
Football League Cup 1967/68, Third round |
| 11.10.1967 | | Stoke City | – | Ipswich Town | | 2:1 |
| |
Football League Cup 1966/67, Third round |
| 04.10.1966 | | Birmingham City | – | Ipswich Town | | 2:1 |
| |
Football League Cup 1965/66, Fifth Round |
| 17.11.1965 | | Cardiff City | – | Ipswich Town | | 2:1 |
| |
Football League Cup 1964/65, Second round |
| 23.09.1964 | | Coventry City | – | Ipswich Town | | 4:1 |
| |
Football League Cup 1963/64, Second round |
| 03.10.1963 | | Walsall | – | Ipswich Town | | 1:0 * |
| |
Football League Cup 1961/62, Fourth Round |
| 11.12.1961 | | Blackburn Rovers | – | Ipswich Town | | 4:1 |
| |
Football League Cup 1960/61, First Round |
| 11.10.1960 | | Ipswich Town | – | Barnsley | | 0:2 |
| |
