Football League Cup 1999/00, First Round |
 | 10.08.1999 |  | Chester City | – | Port Vale | | 2:1 (1:1) |
| Chester |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Port Vale | – | Chester City | | 1:2 (0:2) |
| Stoke-on-Trent |
Football League Cup 1995/96, First Round |
| 22.08.1995 | | Wigan Athletic | – | Chester City | | 1:3 (0:2) |
| Wigan |
Football League Cup 1995/96, First Round |
| 15.08.1995 | | Chester City | – | Wigan Athletic | | 4:1 (2:0) |
| Chester |
Football League Cup 1991/92, First Round |
| 20.08.1991 | | Chester City | – | Lincoln City | | 1:0 (0:0) |
| Macclesfield |
Football League Cup 1990/91, First Round |
| 04.09.1990 | | Chester City | – | Preston North End | | 5:1 aet |
| Macclesfield |
Football League Cup 1988/89, First Round |
| 07.09.1988 | | Chester City | – | Bolton Wanderers | | 3:1 |
| Chester |
Football League Cup 1987/88, First Round |
| 26.08.1987 | | Chester City | – | Blackpool | | 1:0 |
| Chester |
Football League Cup 1986/87, First Round |
| 27.08.1986 | | Derby County | – | Chester City | | 0:1 |
| Derby |
Football League Cup 1985/86, First Round |
| 28.08.1985 | | Tranmere Rovers | – | Chester City | | 1:3 |
| |
Football League Cup 1983/84, Second round |
| 05.10.1983 | | Leeds United | – | Chester City | | 0:1 |
| |
Football League Cup 1983/84, First Round |
| 14.09.1983 | | Chester City | – | Bolton Wanderers | | 3:0 aet,
pen. 2:0 |
| |
Football League Cup 1979/80, First Round |
| 11.08.1979 | | Chester City | – | Walsall | | 2:1 |
| |
Football League Cup 1978/79, Second round |
| 30.08.1978 | | Chester City | – | Coventry City | | 2:1 |
| |
Football League Cup 1978/79, First Round |
| 12.08.1978 | | Port Vale | – | Chester City | | 0:3 |
| |
Football League Cup 1977/78, First Round |
| 17.08.1977 | | Chester | – | Burnley | | 1:0 |
| |
Football League Cup 1976/77, First Round |
| 14.08.1976 | | Chester | – | Hereford United | | 2:0 |
| |
Football League Cup 1974/75, Fifth Round |
| 18.12.1974 | | Chester City | – | Newcastle United | | 1:0 * |
| |
Football League Cup 1974/75, Fourth Round |
| 13.11.1974 | | Chester City | – | Leeds United | | 3:0 |
| |
Football League Cup 1974/75, Third round |
| 09.10.1974 | | Chester City | – | Preston North End | | 1:0 |
| |
Football League Cup 1974/75, Second round |
| 11.09.1974 | | Chester City | – | Blackpool | | 3:1 |
| |
Football League Cup 1974/75, First Round |
| 21.08.1974 | | Chester City | – | Walsall | | 2:1 |
| |
Football League Cup 1972/73, First Round |
| 16.08.1972 | | Chester City | – | Shrewsbury Town | | 4:3 |
| |
Football League Cup 1970/71, First Round |
| 19.08.1970 | | Chester | – | Shrewsbury Town | | 2:1 |
| |
Football League Cup 1964/65, Second round |
| 23.09.1964 | | Chester | – | Derby County | | 5:4 |
| |
Football League Cup 1964/65, First Round |
| 02.09.1964 | | Chester | – | Wrexham |  | 3:0 |
| |
Football League Cup 1962/63, Second round |
| 10.10.1962 | | Mansfield Town | – | Chester | | 0:1 * |
| |
Football League Cup 1962/63, First Round |
| 05.09.1962 | | Chester | – | Stockport County | | 2:0 |
| |
