Football League Cup 2022/23, Second Round |
 | 23.08.2022 | | Newport County | – | Portsmouth | | 3:2 (1:2) |
| Newport |
Football League Cup 2021/22, First Round |
| 10.08.2021 | | Millwall | – | Portsmouth | | 2:1 (2:1) |
| London |
Football League Cup 2020/21, Second round |
| 17.09.2020 | | Brighton & Hove Albion | – | Portsmouth | | 4:0 (1:0) * |
| Brighton & Hove |
Football League Cup 2019/20, Third round |
| 24.09.2019 | | Portsmouth | – | Southampton | | 0:4 (0:2) |
| Portsmouth |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Portsmouth | – | AFC Wimbledon | | 1:2 (0:0) |
| Portsmouth |
Football League Cup 2017/18, First Round |
| 08.08.2017 | | Cardiff City | – | Portsmouth | | 2:1 aet
(0:1, 1:1) |
| Cardiff |
Football League Cup 2016/17, First Round |
| 09.08.2016 | | Coventry City | – | Portsmouth | | 3:2 aet
(0:1, 2:2) |
| Coventry |
Football League Cup 2015/16, Second round |
| 25.08.2015 | | Portsmouth | – | Reading | | 1:2 (1:0) |
| Portsmouth |
Football League Cup 2014/15, Second round |
| 27.08.2014 | | Stoke City | – | Portsmouth | | 3:0 (1:0) |
| Stoke-on-Trent |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | AFC Bournemouth | – | Portsmouth | | 1:0 (0:0) |
| Bournemouth |
Football League Cup 2012/13, First Round |
| 14.08.2012 | | Plymouth Argyle | – | Portsmouth | | 3:0 (1:0) |
| Plymouth |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Portsmouth | – | Barnet | | 0:1 (0:0) |
| Portsmouth |
Football League Cup 2010/11, Third round |
| 21.09.2010 | | Portsmouth | – | Leicester City | | 1:2 (0:2) |
| Portsmouth |
Football League Cup 2009/10, Fifth Round |
| 01.12.2009 | | Portsmouth | – | Aston Villa | | 2:4 (1:2) |
| Portsmouth |
Football League Cup 2008/09, Third round |
| 24.09.2008 | | Portsmouth | – | Chelsea | | 0:4 (0:2) |
| Portsmouth |
Football League Cup 2007/08, Fourth Round |
| 31.10.2007 | | Portsmouth | – | Blackburn Rovers | | 1:2 (0:1) |
| Portsmouth |
Football League Cup 2006/07, Third round |
| 25.10.2006 | | Newcastle United | – | Portsmouth | | 3:0 (0:0) |
| Newcastle upon Tyne |
Football League Cup 2005/06, Second round |
| 20.09.2005 | | Gillingham | – | Portsmouth | | 3:2 aet
(1:1, 2:2) |
| Gillingham |
Football League Cup 2004/05, Fifth Round |
| 30.11.2004 | | Watford | – | Portsmouth | | 3:0 (1:0) |
| Watford |
Football League Cup 2003/04, Fourth Round |
| 02.12.2003 | | Southampton | – | Portsmouth | | 2:0 (1:0) |
| Southampton |
Football League Cup 2002/03, Second round |
| 01.10.2002 | | Portsmouth | – | Wimbledon | | 1:3 (1:2) |
| Portsmouth |
Football League Cup 2001/02, First Round |
| 21.08.2001 | | Portsmouth | – | Colchester United | | 1:2 (0:0) |
| Portsmouth |
Football League Cup 2000/01, Second round |
| 19.09.2000 | | Blackburn Rovers | – | Portsmouth | | 4:0 (2:0) |
| Blackburn |
Football League Cup 1999/00, Second round |
| 22.09.1999 | | Blackburn Rovers | – | Portsmouth | | 3:1 (0:1) |
| Blackburn |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Portsmouth | – | Blackburn Rovers | | 0:3 (0:0) |
| Portsmouth |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Wimbledon | – | Portsmouth | | 4:1 aet
(1:1, 2:1) |
| London |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Portsmouth | – | Peterborough United | | 1:2 (1:1) |
| Portsmouth |
Football League Cup 1996/97, Second round |
| 18.09.1996 | | Wimbledon | – | Portsmouth | | 1:0 (0:0) |
| London |
Football League Cup 1996/97, First Round |
| 04.09.1996 | | Leyton Orient | – | Portsmouth | | 1:0 (0:0) |
| London |
Football League Cup 1995/96, First Round |
| 22.08.1995 | | Cardiff City | – | Portsmouth | | 1:0 (0:0) |
| Cardiff |
Football League Cup 1995/96, First Round |
| 16.08.1995 | | Portsmouth | – | Cardiff City | | 0:2 (0:1) |
| Portsmouth |
Football League Cup 1994/95, Third round |
| 26.10.1994 | | Portsmouth | – | Derby County | | 0:1 (0:0) |
| Portsmouth |
Football League Cup 1993/94, Fifth Round |
| 26.01.1994 | | Portsmouth | – | Manchester United | | 0:1 (0:1) |
| Portsmouth |
Football League Cup 1992/93, Third round |
| 27.10.1992 | | Portsmouth | – | Ipswich Town | | 0:1 (0:1) |
| Portsmouth |
Football League Cup 1991/92, Third round |
| 30.10.1991 | | Manchester United | – | Portsmouth | | 3:1 (0:0) |
| Manchester |
Football League Cup 1990/91, Third round |
| 06.11.1990 | | Portsmouth | – | Chelsea | | 2:3 * |
| Portsmouth |
Football League Cup 1989/90, Second round |
| 20.09.1989 | | Portsmouth | – | Manchester United | | 2:3 |
| Portsmouth |
Football League Cup 1989/90, First Round |
| 23.08.1989 | | Bristol Rovers | – | Portsmouth | | 1:0 |
| Bath |
Football League Cup 1988/89, Second round |
| 12.10.1988 | | Scarborough | – | Portsmouth | | 3:1 |
| Scarborough |
Football League Cup 1987/88, Second round |
| 07.10.1987 | | Portsmouth | – | Swindon Town | | 1:3 |
| Portsmouth |
Football League Cup 1987/88, Second round |
| 22.09.1987 | | Swindon Town | – | Portsmouth | | 3:1 |
| Swindon |
Football League Cup 1986/87, Third round |
| 29.10.1986 | | Bradford City | – | Portsmouth | | 3:1 |
| Bradford |
Football League Cup 1985/86, Fifth Round |
| 22.01.1986 | | Oxford United | – | Portsmouth | | 3:1 |
| |
Football League Cup 1984/85, Second round |
| 10.10.1984 | | Nottingham Forest | – | Portsmouth | | 3:0 aet |
| |
Football League Cup 1984/85, First Round |
| 04.09.1984 | | Wimbledon | – | Portsmouth | | 1:0 |
| |
Football League Cup 1983/84, Second round |
| 26.10.1983 | | Aston Villa | – | Portsmouth | | 3:2 aet
(0:1, 2:2) |
| Birmingham |
Football League Cup 1983/84, First Round |
| 31.08.1983 | | Hereford United | – | Portsmouth | | 3:2 |
| |
Football League Cup 1982/83, First Round |
| 31.08.1982 | | Crystal Palace | – | Portsmouth | | 2:0 |
| |
Football League Cup 1981/82, Second round |
| 06.10.1981 | | Queens Park Rangers | – | Portsmouth | | 5:0 |
| |
Football League Cup 1980/81, Fourth Round |
| 28.10.1980 | | Liverpool | – | Portsmouth | | 4:1 |
| Liverpool |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Oldham Athletic | – | Portsmouth | | 3:2 |
| |
Football League Cup 1979/80, First Round |
| 14.08.1979 | | Swindon Town | – | Portsmouth | | 2:0 |
| |
Football League Cup 1979/80, First Round |
| 11.08.1979 | | Portsmouth | – | Swindon Town | | 1:2 |
| |
Football League Cup 1978/79, First Round |
| 15.08.1978 | | Swindon Town | – | Portsmouth | | 4:2 |
| |
Football League Cup 1977/78, Third round |
| 01.11.1977 | | Swindon Town | – | Portsmouth | | 4:3 * |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | Newport County | – | Portsmouth | | 3:2 |
| |
Football League Cup 1976/77, First Round |
| 17.08.1976 | | Portsmouth | – | Crystal Palace | | 0:1 |
| |
Football League Cup 1975/76, Second round |
| 17.09.1975 | | Leicester City | – | Portsmouth | | 1:0 aet * |
| |
Football League Cup 1974/75, Second round |
| 11.09.1974 | | Portsmouth | – | Derby County | | 1:5 |
| |
Football League Cup 1973/74, Second round |
| 09.10.1973 | | Plymouth Argyle | – | Portsmouth | | 4:0 |
| |
Football League Cup 1972/73, Second round |
| 06.09.1972 | | Portsmouth | – | Chesterfield | | 0:1 |
| |
Football League Cup 1971/72, First Round |
| 17.08.1971 | | Bournemouth | – | Portsmouth | | 2:1 |
| |
Football League Cup 1970/71, Third round |
| 07.10.1970 | | Manchester United | – | Portsmouth | | 1:0 |
| Manchester |
Football League Cup 1969/70, First Round |
| 13.08.1969 | | Brighton & Hove Albion | – | Portsmouth | | 1:0 |
| |
Football League Cup 1968/69, Second round |
| 03.09.1968 | | Coventry City | – | Portsmouth | | 2:0 |
| |
Football League Cup 1967/68, Third round |
| 11.10.1967 | | Darlington | – | Portsmouth | | 4:1 |
| |
Football League Cup 1966/67, Second round |
| 13.09.1966 | | Swindon Town | – | Portsmouth | | 4:1 |
| |
Football League Cup 1965/66, Third round |
| 13.10.1965 | | Cardiff City | – | Portsmouth | | 2:0 |
| |
Football League Cup 1964/65, Third round |
| 20.10.1964 | | Northampton Town | – | Portsmouth | | 2:1 |
| |
Football League Cup 1963/64, Fourth Round |
| 13.11.1963 | | Notts County | – | Portsmouth | | 3:2 |
| |
Football League Cup 1962/63, Fourth Round |
| 21.11.1962 | | Sunderland | – | Portsmouth | | 2:1 * |
| Sunderland |
Football League Cup 1961/62, Third round |
| 13.11.1961 | | Sheffield United | – | Portsmouth | | 1:0 |
| |
Football League Cup 1960/61, Fifth Round |
| 13.02.1961 | | Rotherham United | – | Portsmouth | | 3:0 |
| |
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