Football League Cup 2023/24, Third Round |
 | 26.09.2023 | | Ipswich Town | – | Wolverhampton Wanderers | | 3:2 (2:2) |
| Ipswich |
Football League Cup 2023/24, First Round |
| 09.08.2023 | | Ipswich Town | – | Bristol Rovers | | 2:0 (1:0) |
| Ipswich |
Football League Cup 2020/21, First Round |
| 05.09.2020 | | Ipswich Town | – | Bristol Rovers | | 3:0 (2:0) * |
| Ipswich |
Football League Cup 2017/18, First Round |
| 08.08.2017 | | Luton Town | – | Ipswich Town | | 0:2 (0:1) |
| Luton |
Football League Cup 2015/16, Second round |
| 25.08.2015 | | Doncaster Rovers | – | Ipswich Town | | 1:4 aet
(1:0, 1:1) |
| Doncaster |
Football League Cup 2015/16, First Round |
| 11.08.2015 | | Ipswich Town | – | Stevenage | | 2:1 (0:1) |
| Ipswich |
Football League Cup 2012/13, First Round |
| 14.08.2012 | | Ipswich Town | – | Bristol Rovers | | 3:1 (1:1) |
| Ipswich |
Football League Cup 2010/11, Semifinals |
| 12.01.2011 | | Ipswich Town | – | Arsenal | | 1:0 (0:0) |
| Ipswich |
Football League Cup 2010/11, Fifth Round |
| 01.12.2010 | | Ipswich Town | – | West Bromwich Albion | | 1:0 (0:0) |
| Ipswich |
Football League Cup 2010/11, Fourth Round |
| 26.10.2010 | | Ipswich Town | – | Northampton Town | | 3:1 (2:1) |
| Ipswich |
Football League Cup 2010/11, Third round |
| 21.09.2010 | | Millwall | – | Ipswich Town | | 1:2 (0:2) |
| London |
Football League Cup 2010/11, Second round |
| 24.08.2010 | | Crewe Alexandra | – | Ipswich Town | | 0:1 aet
(0:0) |
| Crewe |
Football League Cup 2010/11, First Round |
| 10.08.2010 | | Exeter City | – | Ipswich Town | | 2:3 aet
(0:0, 2:2) |
| Exeter |
Football League Cup 2008/09, Second round |
| 26.08.2008 | | Ipswich Town | – | Colchester United | | 2:1 (1:0) |
| Ipswich |
Football League Cup 2008/09, First Round |
| 12.08.2008 | | Ipswich Town | – | Leyton Orient | | 4:1 (3:0) |
| Ipswich |
Football League Cup 2004/05, First Round |
| 24.08.2004 | | Ipswich Town | – | Brentford | | 2:0 (0:0) |
| Ipswich |
Football League Cup 2003/04, First Round |
| 13.08.2003 | | Ipswich Town | – | Kidderminster Harriers | | 1:0 aet
(0:0) |
| Ipswich |
Football League Cup 2002/03, Third round |
| 06.11.2002 | | Ipswich Town | – | Middlesbrough | | 3:1 (3:0) |
| Ipswich |
Football League Cup 2002/03, Second round |
| 24.09.2002 | | Ipswich Town | – | Brighton & Hove Albion | | 3:1 (3:1) |
| Ipswich |
Football League Cup 2001/02, Third round |
| 09.10.2001 | | Crewe Alexandra | – | Ipswich Town | | 2:3 (1:2) |
| Crewe |
Football League Cup 2000/01, Semifinals |
| 09.01.2001 | | Ipswich Town | – | Birmingham City | | 1:0 (1:0) |
| Ipswich |
Football League Cup 2000/01, Fifth Round |
| 19.12.2000 | | Manchester City | – | Ipswich Town | | 1:2 aet
(1:0, 1:1) |
| Manchester |
Football League Cup 2000/01, Fourth Round |
| 28.11.2000 | | Ipswich Town | – | Coventry City | | 2:1 (1:0) |
| Ipswich |
Football League Cup 2000/01, Third round |
| 01.11.2000 | | Arsenal | – | Ipswich Town | | 1:2 (1:1) |
| London |
Football League Cup 2000/01, Second round |
| 26.09.2000 | | Ipswich Town | – | Millwall | | 5:0 aet
(0:0, 2:0) |
| Ipswich |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Ipswich Town | – | Brentford | | 2:0 (1:0) |
| Ipswich |
Football League Cup 1999/00, First Round |
| 11.08.1999 | | Brentford | – | Ipswich Town | | 0:2 (0:0) |
| Brentford |
Football League Cup 1998/99, Second round |
| 15.09.1998 | | Ipswich Town | – | Luton Town | | 2:1 (0:0) |
| Ipswich |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Ipswich Town | – | Exeter City | | 5:1 (3:1) |
| Ipswich |
Football League Cup 1997/98, Fourth Round |
| 18.11.1997 | | Oxford United | – | Ipswich Town | | 1:2 aet
(0:0, 1:1) |
| Oxford |
Football League Cup 1997/98, Third round |
| 14.10.1997 | | Ipswich Town | – | Manchester United | | 2:0 (2:0) |
| Ipswich |
Football League Cup 1997/98, Second round |
| 23.09.1997 | | Torquay United | – | Ipswich Town | | 0:3 (0:1) |
| Torquay |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Ipswich Town | – | Charlton Athletic | | 3:1 (2:0) |
| Ipswich |
Football League Cup 1997/98, First Round |
| 13.08.1997 | | Charlton Athletic | – | Ipswich Town | | 0:1 (0:1) |
| London |
Football League Cup 1996/97, Fourth Round |
| 26.11.1996 | | Ipswich Town | – | Gillingham | | 1:0 (0:0) |
| Ipswich |
Football League Cup 1996/97, Third round |
| 22.10.1996 | | Ipswich Town | – | Crystal Palace | | 4:1 (2:1) |
| Ipswich |
Football League Cup 1996/97, Second round |
| 24.09.1996 | | Ipswich Town | – | Fulham | | 4:2 (1:1) |
| Ipswich |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | Bournemouth | – | Ipswich Town | | 0:3 (0:1) |
| Bournemouth |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Ipswich Town | – | Bournemouth | | 2:1 (1:0) |
| Ipswich |
Football League Cup 1993/94, Second round |
| 05.10.1993 | | Cambridge United | – | Ipswich Town | | 0:2 (0:0) |
| Cambridge |
Football League Cup 1993/94, Second round |
| 21.09.1993 | | Ipswich Town | – | Cambridge United | | 2:1 (1:0) |
| Ipswich |
Football League Cup 1992/93, Fourth Round |
| 15.12.1992 | | Ipswich Town | – | Aston Villa | | 1:0 (0:0) * |
| Ipswich |
Football League Cup 1992/93, Third round |
| 27.10.1992 | | Portsmouth | – | Ipswich Town | | 0:1 (0:1) |
| Portsmouth |
Football League Cup 1992/93, Second round |
| 06.10.1992 | | Ipswich Town | – | Wigan Athletic | | 4:0 (2:0) |
| Ipswich |
Football League Cup 1990/91, Second round |
| 09.10.1990 | | Ipswich Town | – | Shrewsbury Town | | 3:0 |
| Ipswich |
Football League Cup 1988/89, Third round |
| 01.11.1988 | | Ipswich Town | – | Leyton Orient | | 2:0 |
| Ipswich |
Football League Cup 1988/89, Second round |
| 11.10.1988 | | Ipswich Town | – | Port Vale | | 3:0 |
| Ipswich |
Football League Cup 1987/88, Third round |
| 27.10.1987 | | Ipswich Town | – | Southend United | | 1:0 |
| Ipswich |
Football League Cup 1987/88, Second round |
| 07.10.1987 | | Northampton Town | – | Ipswich Town | | 2:4 aet |
| Northampton |
Football League Cup 1986/87, Second round |
| 07.10.1986 | | Ipswich Town | – | Scunthorpe United | | 2:0 |
| Ipswich |
Football League Cup 1986/87, Second round |
| 23.09.1986 | | Scunthorpe United | – | Ipswich Town | | 1:2 |
| Scunthorpe |
Football League Cup 1985/86, Fourth Round |
| 26.11.1985 | | Ipswich Town | – | Swindon Town | | 6:1 |
| |
Football League Cup 1985/86, Third round |
| 29.10.1985 | | Grimsby Town | – | Ipswich Town | | 0:2 |
| |
Football League Cup 1985/86, Second round |
| 08.10.1985 | | Darlington | – | Ipswich Town | | 1:4 |
| |
Football League Cup 1985/86, Second round |
| 24.09.1985 | | Ipswich Town | – | Darlington | | 3:1 |
| |
Football League Cup 1984/85, Semifinals |
| 23.02.1985 | | Ipswich Town | – | Norwich City | | 1:0 |
| Ipswich |
Football League Cup 1984/85, Fifth Round |
| 28.01.1985 | | Queens Park Rangers | – | Ipswich Town | | 1:2 * |
| |
Football League Cup 1984/85, Fourth Round |
| 20.11.1984 | | Ipswich Town | – | Oxford United | | 2:1 |
| |
Football League Cup 1984/85, Third round |
| 07.11.1984 | | Newcastle United | – | Ipswich Town | | 1:2 * |
| |
Football League Cup 1984/85, Second round |
| 25.09.1984 | | Ipswich Town | – | Derby County | | 4:2 |
| |
Football League Cup 1983/84, Third round |
| 09.11.1983 | | Ipswich Town | – | Queens Park Rangers | | 3:2 |
| |
Football League Cup 1983/84, Second round |
| 26.10.1983 | | Blackburn Rovers | – | Ipswich Town | | 1:2 |
| |
Football League Cup 1983/84, Second round |
| 05.10.1983 | | Ipswich Town | – | Blackburn Rovers | | 4:3 |
| |
Football League Cup 1981/82, Fifth Round |
| 18.01.1982 | | Ipswich Town | – | Watford | | 2:1 |
| |
Football League Cup 1981/82, Fourth Round |
| 15.12.1981 | | Everton | – | Ipswich Town | | 2:3 |
| |
Football League Cup 1981/82, Third round |
| 02.12.1981 | | Bradford City | – | Ipswich Town | | 2:3 aet * |
| |
Football League Cup 1981/82, Second round |
| 27.10.1981 | | Ipswich Town | – | Leeds United | | 3:0 |
| |
Football League Cup 1981/82, Second round |
| 07.10.1981 | | Leeds United | – | Ipswich Town | | 0:1 |
| |
Football League Cup 1980/81, Third round |
| 08.10.1980 | | Norwich City | – | Ipswich Town | | 1:3 * |
| |
Football League Cup 1980/81, Second round |
| 02.09.1980 | | Ipswich Town | – | Middlesbrough | | 3:0 |
| |
Football League Cup 1977/78, Third round |
| 25.10.1977 | | Burnley | – | Ipswich Town | | 1:2 |
| |
Football League Cup 1977/78, Second round |
| 30.08.1977 | | Ipswich Town | – | Northampton Town | | 5:0 |
| |
Football League Cup 1974/75, Fourth Round |
| 12.11.1974 | | Ipswich Town | – | Stoke City | | 2:1 |
| |
Football League Cup 1974/75, Third round |
| 08.10.1974 | | Ipswich Town | – | Hereford United | | 4:1 |
| |
Football League Cup 1974/75, Second round |
| 10.09.1974 | | Coventry City | – | Ipswich Town | | 1:2 |
| |
Football League Cup 1973/74, Third round |
| 14.11.1973 | | Ipswich Town | – | Fulham | | 2:1 * |
| |
Football League Cup 1973/74, Second round |
| 08.10.1973 | | Ipswich Town | – | Leeds United | | 2:0 |
| |
Football League Cup 1972/73, Second round |
| 05.09.1972 | | Newport County | – | Ipswich Town | | 0:3 |
| |
Football League Cup 1969/70, Second round |
| 03.09.1969 | | Ipswich Town | – | Colchester United | | 4:0 |
| |
Football League Cup 1967/68, Second round |
| 12.09.1967 | | Ipswich Town | – | Southampton | | 5:2 |
| |
Football League Cup 1966/67, Second round |
| 13.09.1966 | | Brentford | – | Ipswich Town | | 2:4 |
| |
Football League Cup 1965/66, Fourth Round |
| 03.11.1965 | | Ipswich Town | – | Darlington | | 2:0 |
| |
Football League Cup 1965/66, Third round |
| 20.10.1965 | | Ipswich Town | – | Workington | | 3:1 * |
| |
Football League Cup 1965/66, Second round |
| 21.09.1965 | | Brighton & Hove Albion | – | Ipswich Town | | 1:2 |
| |
Football League Cup 1961/62, Third round |
| 21.11.1961 | | Aston Villa | – | Ipswich Town | | 2:3 (0:2) |
| Birmingham |
Football League Cup 1961/62, Second round |
| 24.10.1961 | | Ipswich Town | – | Swansea Town | | 3:2 * |
| |
Football League Cup 1961/62, First Round |
| 11.09.1961 | | Ipswich Town | – | Manchester City | | 4:2 |
| |
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