Football League Cup 2024/25, Second Round |
| 28.08.2024 | | AFC Wimbledon | | Ipswich Town | | 2:2 (1:1), pen. 4:2 |
| London |
Football League Cup 2023/24, Fourth Round |
| 01.11.2023 | | Ipswich Town | | Fulham | | 1:3 (0:1) |
| Ipswich |
Football League Cup 2023/24, Third Round |
| 26.09.2023 | | Ipswich Town | | Wolverhampton Wanderers | | 3:2 (2:2) |
| Ipswich |
Football League Cup 2023/24, Second Round |
| 29.08.2023 | | Reading | | Ipswich Town | | 2:2 (1:1), pen. 1:3 |
| Reading |
Football League Cup 2023/24, First Round |
| 09.08.2023 | | Ipswich Town | | Bristol Rovers | | 2:0 (1:0) |
| 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 2020/21, First Round |
| 05.09.2020 | | Ipswich Town | | Bristol Rovers | | 3:0 (2:0) * |
| Ipswich |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Luton Town | | Ipswich Town | | 3:1 (2:0) |
| Luton |
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 2017/18, Second round |
| 22.08.2017 | | Crystal Palace | | Ipswich Town | | 2:1 (0:0) |
| London |
Football League Cup 2017/18, First Round |
| 08.08.2017 | | Luton Town | | Ipswich Town | | 0:2 (0:1) |
| Luton |
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 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 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 2012/13, First Round |
| 14.08.2012 | | Ipswich Town | | Bristol Rovers | | 3:1 (1:1) |
| Ipswich |
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 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 2009/10, Second round |
| 25.08.2009 | | Peterborough United | | Ipswich Town | | 2:1 (1:1) |
| Peterborough |
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 2008/09, Third round |
| 24.09.2008 | | Ipswich Town | | Wigan Athletic | | 1:4 (0:0) |
| Ipswich |
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 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 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 2004/05, First Round |
| 24.08.2004 | | Ipswich Town | | Brentford | | 2:0 (0:0) |
| Ipswich |
Football League Cup 2003/04, Second round |
| 23.09.2003 | | Notts County | | Ipswich Town | | 2:1 (2:1) |
| Nottingham |
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, Fourth Round |
| 04.12.2002 | | Liverpool | | Ipswich Town | | 1:1 aet (0:1, 1:1), pen. 5:4 |
| Liverpool |
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, Fourth Round |
| 27.11.2001 | | Newcastle United | | Ipswich Town | | 4:1 (4:0) |
| Newcastle upon Tyne |
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 |
| 31.01.2001 | | Birmingham City | | Ipswich Town | | 4:1 aet (1:0, 1:1) |
| Birmingham |
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 2000/01, Second round |
| 19.09.2000 | | Millwall | | Ipswich Town | | 2:0 (1:0) |
| London |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Ipswich Town | | Crewe Alexandra | | 1:1 (1:0) |
| Ipswich |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Crewe Alexandra | | Ipswich Town | | 2:1 (0:1) |
| Crewe |
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 |
| 22.09.1998 | | Luton Town | | Ipswich Town | | 4:2 aet (0:1, 2:1) |
| Luton |
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 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, 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, Second round |
| 16.09.1997 | | Ipswich Town | | Torquay United | | 1:1 (0:1) |
| Ipswich |
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, Fifth Round |
| 21.01.1997 | | Ipswich Town | | Leicester City | | 0:1 (0:1) |
| Ipswich |
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, Second round |
| 17.09.1996 | | Fulham | | Ipswich Town | | 1:1 (1:0) |
| London |
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 1995/96, Second round |
| 03.10.1995 | | Ipswich Town | | Stockport County | | 1:2 aet (1:0, 1:1) |
| Ipswich |
Football League Cup 1995/96, Second round |
| 19.09.1995 | | Stockport County | | Ipswich Town | | 1:1 (1:1) |
| Stockport |
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 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, Fifth Round |
| 03.02.1993 | | Sheffield Wednesday | | Ipswich Town | | 1:0 (0:0) * |
| Sheffield |
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 |
| 15.12.1992 | | Ipswich Town | | Aston Villa | | 1:0 (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, 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 1992/93, Second round |
| 22.09.1992 | | Wigan Athletic | | Ipswich Town | | 2:2 (0:1) |
| Wigan |
Football League Cup 1991/92, Second round |
| 08.10.1991 | | Ipswich Town | | Derby County | | 0:2 (0:2) |
| Ipswich |
Football League Cup 1991/92, Second round |
| 25.09.1991 | | Derby County | | Ipswich Town | | 0:0 |
| Derby |
Football League Cup 1990/91, Third round |
| 30.10.1990 | | Ipswich Town | | Southampton | | 0:2 |
| Ipswich |
Football League Cup 1990/91, Second round |
| 09.10.1990 | | Ipswich Town | | Shrewsbury Town | | 3:0 |
| Ipswich |
Football League Cup 1990/91, Second round |
| 25.09.1990 | | Shrewsbury Town | | Ipswich Town | | 1:1 |
| Shrewsbury |
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, 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 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 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 1987/88, Second round |
| 22.09.1987 | | Ipswich Town | | Northampton Town | | 1:1 |
| Ipswich |
Football League Cup 1986/87, Third round |
| 28.10.1986 | | Cambridge United | | Ipswich Town | | 1:0 |
| Cambridge |
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, Fifth Round |
| 21.01.1986 | | Liverpool | | Ipswich Town | | 3:0 |
| Liverpool |
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 |
| 06.03.1985 | | Norwich City | | Ipswich Town | | 2:0 |
| Norwich |
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, Fifth Round |
| 23.01.1985 | | Ipswich Town | | Queens Park Rangers | | 0:0 |
| |
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, 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 1984/85, Second round |
| 25.09.1984 | | Ipswich Town | | Derby County | | 4:2 |
| |
Football League Cup 1983/84, Fourth Round |
| 30.11.1983 | | Ipswich Town | | Norwich City | | 0:1 |
| |
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 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 |
| 09.02.1982 | | Liverpool | | Ipswich Town | | 2:2 |
| Liverpool |
Football League Cup 1981/82, Semifinals |
| 02.02.1982 | | Ipswich Town | | Liverpool | | 0:2 |
| |
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, Third round |
| 10.11.1981 | | Ipswich Town | | Bradford City | | 1:1 |
| |
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, Fourth Round |
| 28.10.1980 | | Birmingham City | | Ipswich Town | | 2:1 |
| |
Football League Cup 1980/81, Third round |
| 08.10.1980 | | Norwich City | | Ipswich Town | | 1:3 * |
| |
Football League Cup 1980/81, Third round |
| 23.09.1980 | | Ipswich Town | | Norwich City | | 1:1 |
| |
Football League Cup 1980/81, Second round |
| 02.09.1980 | | Ipswich Town | | Middlesbrough | | 3:0 |
| |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Middlesbrough | | Ipswich Town | | 3:1 |
| |
Football League Cup 1979/80, Second round |
| 04.09.1979 | | Coventry City | | Ipswich Town | | 0:0 |
| |
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 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 1976/77, Second round |
| 07.09.1976 | | Brighton & Hove Albion | | Ipswich Town | | 2:1 * |
| |
Football League Cup 1976/77, Second round |
| 31.08.1976 | | Ipswich Town | | Brighton & Hove Albion | | 0:0 |
| |
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 1974/75, Fifth Round |
| 04.12.1974 | | Norwich City | | Ipswich Town | | 1:1 |
| |
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, Fourth Round |
| 21.11.1973 | | Ipswich Town | | Birmingham City | | 1:3 |
| |
Football League Cup 1973/74, Third round |
| 14.11.1973 | | Ipswich Town | | Fulham | | 2:1 * |
| |
Football League Cup 1973/74, Third round |
| 31.10.1973 | | Fulham | | Ipswich Town | | 2:2 |
| |
Football League Cup 1973/74, Second round |
| 08.10.1973 | | Ipswich Town | | Leeds United | | 2:0 |
| |
Football League Cup 1972/73, Third round |
| 03.10.1972 | | Ipswich Town | | Stoke City | | 1:2 |
| |
Football League Cup 1972/73, Second round |
| 05.09.1972 | | Newport County | | Ipswich Town | | 0:3 |
| |
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 1970/71, Second round |
| 08.09.1970 | | Ipswich Town | | Arsenal | | 0:0 |
| |
Football League Cup 1969/70, Third round |
| 30.09.1969 | | West Bromwich Albion | | Ipswich Town | | 2:0 * |
| West Bromwich |
Football League Cup 1969/70, Third round |
| 24.09.1969 | | Ipswich Town | | West Bromwich Albion | | 1:1 |
| |
Football League Cup 1969/70, Second round |
| 03.09.1969 | | Ipswich Town | | Colchester United | | 4:0 |
| |
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 1967/68, Second round |
| 12.09.1967 | | Ipswich Town | | Southampton | | 5:2 |
| |
Football League Cup 1966/67, Third round |
| 04.10.1966 | | Birmingham City | | Ipswich Town | | 2:1 |
| |
Football League Cup 1966/67, Second round |
| 13.09.1966 | | Brentford | | Ipswich Town | | 2:4 |
| |
Football League Cup 1965/66, Fifth Round |
| 17.11.1965 | | Cardiff City | | Ipswich Town | | 2:1 |
| |
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, Third round |
| 13.10.1965 | | Workington | | Ipswich Town | | 1:1 |
| |
Football League Cup 1965/66, Second round |
| 21.09.1965 | | Brighton & Hove Albion | | Ipswich Town | | 1:2 |
| |
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 1963/64, Second round |
| 25.09.1963 | | Ipswich Town | | Walsall | | 0:0 |
| |
Football League Cup 1961/62, Fourth Round |
| 11.12.1961 | | Blackburn Rovers | | Ipswich Town | | 4:1 |
| |
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, Second round |
| 03.10.1961 | | Swansea Town | | Ipswich Town | | 3:3 |
| |
Football League Cup 1961/62, First Round |
| 11.09.1961 | | Ipswich Town | | Manchester City | | 4:2 |
| |
Football League Cup 1960/61, First Round |
| 11.10.1960 | | Ipswich Town | | Barnsley | | 0:2 |
| |