Football League Cup 2007/08, First Round |
| 14.08.2007 | | Chester City | | Nottingham Forest | | 0:0 aet, pen. 2:4 |
| Chester |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Port Vale | | Chester City | | 4:4 (2:2) |
| Stoke-on-Trent |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Chester City | | Port Vale | | 2:2 (0:1) |
| Chester |
Football League Cup 1993/94, First Round |
| 24.08.1993 | | Chester City | | Sunderland | | 0:0 |
| Chester |
Football League Cup 1992/93, First Round |
| 18.08.1992 | | Stockport County | | Chester City | | 1:1 (1:0) |
| Stockport |
Football League Cup 1985/86, First Round |
| 04.09.1985 | | Chester City | | Tranmere Rovers | | 0:0 |
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Football League Cup 1981/82, First Round |
| 08.09.1981 | | Chester City | | Plymouth Argyle | | 1:1 |
| |
Football League Cup 1980/81, First Round |
| 09.08.1980 | | Chester City | | Stockport County | | 1:1 |
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Football League Cup 1979/80, Second round |
| 05.09.1979 | | Chester City | | Swindon Town | | 1:1 |
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Football League Cup 1979/80, First Round |
| 14.08.1979 | | Walsall | | Chester City | | 0:0 |
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Football League Cup 1978/79, First Round |
| 16.08.1978 | | Chester City | | Port Vale | | 1:1 |
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Football League Cup 1975/76, First Round |
| 27.08.1975 | | Chester City | | Wrexham | | 0:0 |
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Football League Cup 1974/75, Semifinals |
| 15.01.1975 | | Chester City | | Aston Villa | | 2:2 (1:1) |
| Chester |
Football League Cup 1974/75, Fifth Round |
| 04.12.1974 | | Newcastle United | | Chester City | | 0:0 |
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Football League Cup 1972/73, Second round |
| 13.09.1972 | | Chester City | | Southampton | | 2:2 aet * |
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Football League Cup 1972/73, Second round |
| 05.09.1972 | | Southampton | | Chester City | | 0:0 |
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Football League Cup 1971/72, First Round |
| 18.08.1971 | | Tranmere Rovers | | Chester | | 1:1 |
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Football League Cup 1970/71, Second round |
| 09.09.1970 | | Norwich City | | Chester | | 0:0 |
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Football League Cup 1968/69, First Round |
| 26.08.1968 | | Tranmere Rovers | | Chester | | 1:1 aet * |
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Football League Cup 1968/69, First Round |
| 21.08.1968 | | Tranmere Rovers | | Chester | | 2:2 aet * |
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Football League Cup 1968/69, First Round |
| 13.08.1968 | | Chester | | Tranmere Rovers | | 0:0 |
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Football League Cup 1963/64, First Round |
| 04.09.1963 | | Rochdale | | Chester | | 1:1 |
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Football League Cup 1962/63, Second round |
| 26.09.1962 | | Chester | | Mansfield Town | | 2:2 |
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Football League Cup 1960/61, First Round |
| 12.10.1960 | | Chester City | | Leyton Orient | | 2:2 |
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