Football League Cup 2023/24, First Round |
 | 08.08.2023 | | Plymouth Argyle | – | Leyton Orient | | 2:0 (2:0) |
| Plymouth |
Football League Cup 2021/22, First Round |
| 10.08.2021 | | Peterborough United | – | Plymouth Argyle | | 0:4 (0:2) |
| Peterborough |
Football League Cup 2020/21, First Round |
| 05.09.2020 | | Plymouth Argyle | – | Queens Park Rangers | | 3:2 (1:1) * |
| Plymouth |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Plymouth Argyle | – | Leyton Orient | | 2:0 (0:0) |
| Plymouth |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Bristol City | – | Plymouth Argyle | | 0:1 (0:1) |
| Bristol |
Football League Cup 2012/13, First Round |
| 14.08.2012 | | Plymouth Argyle | – | Portsmouth | | 3:0 (1:0) |
| Plymouth |
Football League Cup 2007/08, Second round |
| 28.08.2007 | | Plymouth Argyle | – | Doncaster Rovers | | 2:0 (1:0) |
| Plymouth |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Plymouth Argyle | – | Wycombe Wanderers | | 2:1 (2:0) |
| Plymouth |
Football League Cup 2005/06, First Round |
| 23.08.2005 | | Plymouth Argyle | – | Peterborough United | | 2:1 (2:1) |
| Plymouth |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | Plymouth Argyle | – | Walsall | | 2:1 (1:0) |
| Plymouth |
Football League Cup 1993/94, First Round |
| 24.08.1993 | | Plymouth Argyle | – | Birmingham City | | 2:0 (0:0) |
| Plymouth |
Football League Cup 1992/93, Second round |
| 06.10.1992 | | Plymouth Argyle | – | Luton Town | | 3:2 (1:0) |
| Plymouth |
Football League Cup 1992/93, First Round |
| 25.08.1992 | | Plymouth Argyle | – | West Bromwich Albion | | 2:0 (1:0) |
| Plymouth |
Football League Cup 1990/91, Second round |
| 10.10.1990 | | Wimbledon | – | Plymouth Argyle | | 0:2 |
| London |
Football League Cup 1990/91, Second round |
| 25.09.1990 | | Plymouth Argyle | – | Wimbledon | | 1:0 |
| Plymouth |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Cardiff City | – | Plymouth Argyle | | 0:3 |
| Cardiff |
Football League Cup 1988/89, First Round |
| 06.09.1988 | | Plymouth Argyle | – | Hereford United | | 3:2 |
| Plymouth |
Football League Cup 1988/89, First Round |
| 29.08.1988 | | Hereford United | – | Plymouth Argyle | | 0:3 |
| Hereford |
Football League Cup 1985/86, First Round |
| 20.08.1985 | | Plymouth Argyle | – | Exeter City | | 2:1 |
| |
Football League Cup 1984/85, First Round |
| 04.09.1984 | | Torquay United | – | Plymouth Argyle | | 0:1 |
| |
Football League Cup 1984/85, First Round |
| 27.08.1984 | | Plymouth Argyle | – | Torquay United | | 1:0 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Plymouth Argyle | – | Swindon Town | | 4:1 |
| |
Football League Cup 1982/83, First Round |
| 31.08.1982 | | Plymouth Argyle | – | Bournemouth | | 2:0 |
| |
Football League Cup 1981/82, First Round |
| 15.09.1981 | | Plymouth Argyle | – | Chester City | | 1:0 |
| |
Football League Cup 1979/80, Second round |
| 04.09.1979 | | Chelsea | – | Plymouth Argyle | | 1:2 |
| London |
Football League Cup 1979/80, First Round |
| 14.08.1979 | | Plymouth Argyle | – | Newport County | | 2:0 |
| |
Football League Cup 1978/79, First Round |
| 16.08.1978 | | Torquay United | – | Plymouth Argyle | | 1:2 |
| |
Football League Cup 1975/76, First Round |
| 26.08.1975 | | Bournemouth | – | Plymouth Argyle | | 1:2 |
| |
Football League Cup 1975/76, First Round |
| 19.08.1975 | | Plymouth Argyle | – | Bournemouth | | 2:0 |
| |
Football League Cup 1973/74, Fifth Round |
| 19.12.1973 | | Birmingham City | – | Plymouth Argyle | | 1:2 (1:2) |
| Birmingham |
Football League Cup 1973/74, Fourth Round |
| 20.11.1973 | | Queens Park Rangers | – | Plymouth Argyle | | 0:3 |
| |
Football League Cup 1973/74, Third round |
| 30.10.1973 | | Burnley | – | Plymouth Argyle | | 1:2 |
| |
Football League Cup 1973/74, Second round |
| 09.10.1973 | | Plymouth Argyle | – | Portsmouth | | 4:0 |
| |
Football League Cup 1973/74, First Round |
| 29.08.1973 | | Torquay United | – | Plymouth Argyle | | 0:2 |
| |
Football League Cup 1971/72, First Round |
| 17.08.1971 | | Plymouth Argyle | – | Bristol City | | 1:0 |
| |
Football League Cup 1964/65, Fifth Round |
| 25.11.1964 | | Plymouth Argyle | – | Northampton Town | | 1:0 |
| |
Football League Cup 1964/65, Fourth Round |
| 11.11.1964 | | Plymouth Argyle | – | Stoke City | | 3:1 * |
| |
Football League Cup 1964/65, Third round |
| 14.10.1964 | | Bury | – | Plymouth Argyle | | 0:1 |
| |
Football League Cup 1964/65, Second round |
| 23.09.1964 | | Plymouth Argyle | – | Sheffield United | | 2:1 |
| |
Football League Cup 1960/61, Third round |
| 16.11.1960 | | Plymouth Argyle | – | Birmingham City | | 3:1 * |
| |
Football League Cup 1960/61, Second round |
| 07.11.1960 | | Plymouth Argyle | – | Torquay United | | 2:1 * |
| |
Football League Cup 1960/61, First Round |
| 12.10.1960 | | Plymouth Argyle | – | Southport | | 2:0 |
| |
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