Football League Cup 2023/24, First Round |
 | 08.08.2023 | | Forest Green Rovers | – | Portsmouth | | 1:3 (1:1) |
| Nailsworth |
Football League Cup 2022/23, First Round |
| 09.08.2022 | | Cardiff City | – | Portsmouth | | 0:3 (0:0) |
| Cardiff |
Football League Cup 2019/20, Second round |
| 28.08.2019 | | Queens Park Rangers | – | Portsmouth | | 0:2 (0:0) |
| London |
Football League Cup 2019/20, First Round |
| 06.08.2019 | | Portsmouth | – | Birmingham City | | 3:0 (2:0) |
| Portsmouth |
Football League Cup 2015/16, First Round |
| 12.08.2015 | | Portsmouth | – | Derby County | | 2:1 (0:0) |
| Portsmouth |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Portsmouth | – | Peterborough United | | 1:0 (1:0) |
| Portsmouth |
Football League Cup 2010/11, First Round |
| 09.08.2010 | | Stevenage | – | Portsmouth | | 1:2 (1:2) |
| Stevenage |
Football League Cup 2009/10, Fourth Round |
| 27.10.2009 | | Portsmouth | – | Stoke City | | 4:0 (1:0) |
| Portsmouth |
Football League Cup 2009/10, Third round |
| 22.09.2009 | | Carlisle United | – | Portsmouth | | 1:3 (1:2) |
| Carlisle |
Football League Cup 2009/10, Second round |
| 25.08.2009 | | Portsmouth | – | Hereford United | | 4:1 (3:0) |
| Portsmouth |
Football League Cup 2007/08, Third round |
| 25.09.2007 | | Burnley | – | Portsmouth | | 0:1 (0:0) |
| Burnley |
Football League Cup 2007/08, Second round |
| 28.08.2007 | | Portsmouth | – | Leeds United | | 3:0 (1:0) |
| Portsmouth |
Football League Cup 2006/07, Second round |
| 19.09.2006 | | Mansfield Town | – | Portsmouth | | 1:2 (0:2) |
| Mansfield |
Football League Cup 2004/05, Fourth Round |
| 09.11.2004 | | Cardiff City | – | Portsmouth | | 0:2 (0:0) |
| Cardiff |
Football League Cup 2004/05, Third round |
| 26.10.2004 | | Portsmouth | – | Leeds United | | 2:1 (2:1) |
| Portsmouth |
Football League Cup 2004/05, Second round |
| 21.09.2004 | | Tranmere Rovers | – | Portsmouth | | 0:1 (0:0) |
| Birkenhead |
Football League Cup 2003/04, Third round |
| 29.10.2003 | | Nottingham Forest | – | Portsmouth | | 2:4 aet
(1:0, 2:2) |
| Nottingham |
Football League Cup 2003/04, Second round |
| 23.09.2003 | | Portsmouth | – | Northampton Town | | 5:2 (3:0) |
| Portsmouth |
Football League Cup 2002/03, First Round |
| 10.09.2002 | | Portsmouth | – | Peterborough United | | 2:0 (1:0) |
| Portsmouth |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Portsmouth | – | Cambridge United | | 1:0 (0:0) |
| Portsmouth |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Portsmouth | – | Torquay United | | 3:0 (2:0) |
| Portsmouth |
Football League Cup 1998/99, Second round |
| 15.09.1998 | | Portsmouth | – | Wimbledon | | 2:1 (2:1) |
| Portsmouth |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Portsmouth | – | Plymouth Argyle | | 3:2 (2:1) |
| Portsmouth |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Plymouth Argyle | – | Portsmouth | | 1:3 (1:3) |
| Plymouth |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Portsmouth | – | Leyton Orient | | 2:0 (1:0) |
| Portsmouth |
Football League Cup 1994/95, Second round |
| 20.09.1994 | | Everton | – | Portsmouth | | 2:3 (0:2) |
| Liverpool |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | Cambridge United | – | Portsmouth | | 2:3 (1:1) |
| Cambridge |
Football League Cup 1994/95, First Round |
| 17.08.1994 | | Portsmouth | – | Cambridge United | | 2:0 (2:0) |
| Portsmouth |
Football League Cup 1993/94, Fourth Round |
| 15.12.1993 | | Portsmouth | – | Peterborough United | | 1:0 (0:0) * |
| Portsmouth |
Football League Cup 1993/94, Third round |
| 26.10.1993 | | Portsmouth | – | Swindon Town | | 2:0 (0:0) |
| Portsmouth |
Football League Cup 1993/94, Second round |
| 05.10.1993 | | Portsmouth | – | Rotherham United | | 5:0 (3:0) |
| Portsmouth |
Football League Cup 1992/93, Second round |
| 06.10.1992 | | Portsmouth | – | Blackpool | | 2:0 (1:0) |
| Portsmouth |
Football League Cup 1992/93, Second round |
| 23.09.1992 | | Blackpool | – | Portsmouth | | 0:4 (0:0) |
| Blackpool |
Football League Cup 1991/92, Second round |
| 09.10.1991 | | Oxford United | – | Portsmouth | | 0:1 (0:1) |
| Oxford |
Football League Cup 1991/92, First Round |
| 27.08.1991 | | Gillingham | – | Portsmouth | | 3:4 (1:2) |
| Gillingham |
Football League Cup 1991/92, First Round |
| 20.08.1991 | | Portsmouth | – | Gillingham | | 2:1 (1:0) |
| Portsmouth |
Football League Cup 1990/91, Second round |
| 09.10.1990 | | Portsmouth | – | Cardiff City | | 3:1 aet |
| Portsmouth |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | Portsmouth | – | Bristol Rovers | | 2:0 aet |
| Portsmouth |
Football League Cup 1986/87, Second round |
| 07.10.1986 | | Portsmouth | – | Wrexham | | 2:0 |
| Portsmouth |
Football League Cup 1986/87, Second round |
| 24.09.1986 | | Wrexham | – | Portsmouth | | 1:2 |
| Wrexham |
Football League Cup 1985/86, Fourth Round |
| 10.12.1985 | | Portsmouth | – | Tottenham Hotspur | | 1:0 * |
| Portsmouth |
Football League Cup 1985/86, Third round |
| 29.10.1985 | | Portsmouth | – | Stoke City | | 2:0 |
| |
Football League Cup 1985/86, Second round |
| 08.10.1985 | | Portsmouth | – | Gillingham | | 2:1 |
| |
Football League Cup 1985/86, Second round |
| 24.09.1985 | | Gillingham | – | Portsmouth | | 1:3 |
| |
Football League Cup 1984/85, Second round |
| 25.09.1984 | | Portsmouth | – | Nottingham Forest | | 1:0 |
| |
Football League Cup 1984/85, First Round |
| 28.08.1984 | | Portsmouth | – | Wimbledon | | 3:0 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Portsmouth | – | Hereford United | | 3:1 |
| |
Football League Cup 1981/82, First Round |
| 16.09.1981 | | Portsmouth | – | Southend United | | 4:1 |
| |
Football League Cup 1980/81, Third round |
| 30.09.1980 | | Portsmouth | – | Bristol Rovers | | 2:0 * |
| |
Football League Cup 1980/81, Second round |
| 02.09.1980 | | Portsmouth | – | Oldham Athletic | | 1:0 aet |
| |
Football League Cup 1980/81, First Round |
| 12.08.1980 | | Portsmouth | – | Plymouth Argyle | | 2:1 |
| |
Football League Cup 1980/81, First Round |
| 09.08.1980 | | Plymouth Argyle | – | Portsmouth | | 0:1 |
| |
Football League Cup 1977/78, Second round |
| 30.08.1977 | | Portsmouth | – | Leicester City | | 2:0 |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Portsmouth | – | Newport County | | 3:1 |
| |
Football League Cup 1975/76, First Round |
| 26.08.1975 | | Portsmouth | – | Aldershot | | 2:1 |
| |
Football League Cup 1974/75, First Round |
| 20.08.1974 | | Swindon Town | – | Portsmouth | | 0:1 |
| |
Football League Cup 1973/74, First Round |
| 28.08.1973 | | Portsmouth | – | Southend United | | 2:1 |
| |
Football League Cup 1972/73, First Round |
| 16.08.1972 | | Torquay United | – | Portsmouth | | 1:2 |
| |
Football League Cup 1970/71, Second round |
| 09.09.1970 | | Portsmouth | – | Walsall | | 1:0 |
| |
Football League Cup 1970/71, First Round |
| 19.08.1970 | | Portsmouth | – | Plymouth Argyle | | 2:0 |
| |
Football League Cup 1967/68, Second round |
| 13.09.1967 | | Portsmouth | – | Port Vale | | 3:1 |
| |
Football League Cup 1965/66, Second round |
| 22.09.1965 | | Oldham Athletic | – | Portsmouth | | 1:2 |
| |
Football League Cup 1964/65, Second round |
| 12.10.1964 | | Portsmouth | – | Watford | | 2:1 * |
| |
Football League Cup 1963/64, Third round |
| 04.11.1963 | | Wrexham | – | Portsmouth | | 3:5 |
| |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | Portsmouth | – | Derby County | | 3:2 |
| |
Football League Cup 1962/63, Third round |
| 17.10.1962 | | Portsmouth | – | Coventry City | | 5:1 |
| |
Football League Cup 1962/63, Second round |
| 25.09.1962 | | Brighton & Hove Albion | – | Portsmouth | | 1:5 |
| |
Football League Cup 1961/62, Second round |
| 01.11.1961 | | Derby County | – | Portsmouth | | 2:4 * |
| |
Football League Cup 1961/62, First Round |
| 13.09.1961 | | Barrow | – | Portsmouth | | 0:2 |
| |
Football League Cup 1960/61, Fourth Round |
| 14.12.1960 | | Portsmouth | – | Chelsea | | 1:0 |
| Portsmouth |
Football League Cup 1960/61, Third round |
| 21.11.1960 | | Portsmouth | – | Manchester City | | 2:0 |
| |
Football League Cup 1960/61, Second round |
| 02.11.1960 | | Portsmouth | – | Coventry City | | 2:0 |
| |
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