Football League Cup 2008/09, First Round |
 | 12.08.2008 | | Chester City | – | Leeds United | | 2:5 (1:5) |
| Chester |
Football League Cup 2006/07, First Round |
| 22.08.2006 | | Leeds United | – | Chester City | | 1:0 (0:0) |
| Leeds |
Football League Cup 2005/06, First Round |
| 23.08.2005 | | Wolverhampton Wanderers | – | Chester City | | 5:1 (1:0) |
| Wolverhampton |
Football League Cup 2004/05, First Round |
| 24.08.2004 | | Sunderland | – | Chester City | | 3:0 (1:0) |
| Sunderland |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Aston Villa | – | Chester City | | 5:0 (2:0) |
| Birmingham |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Chester City | – | Aston Villa | | 0:1 (0:0) |
| Chester |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Chester City | – | Sunderland | | 0:1 (0:1) |
| Chester |
Football League Cup 1998/99, Second round |
| 15.09.1998 | | Sunderland | – | Chester City | | 3:0 (2:0) |
| Sunderland |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Carlisle United | – | Chester City | | 3:0 (2:0) |
| Carlisle |
Football League Cup 1997/98, First Round |
| 12.08.1997 | | Chester City | – | Carlisle United | | 1:2 (0:1) |
| Chester |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | Chester City | – | Carlisle United | | 1:3 (0:1) |
| Chester |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Carlisle United | – | Chester City | | 1:0 (1:0) |
| Carlisle |
Football League Cup 1995/96, Second round |
| 04.10.1995 | | Chester City | – | Tottenham Hotspur | | 1:3 (1:2) |
| Chester |
Football League Cup 1995/96, Second round |
| 20.09.1995 | | Tottenham Hotspur | – | Chester City | | 4:0 (3:0) |
| London |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | Chester City | – | Lincoln City | | 2:3 (0:3) |
| Chester |
Football League Cup 1994/95, First Round |
| 16.08.1994 | | Lincoln City | – | Chester City | | 2:0 (1:0) |
| Lincoln |
Football League Cup 1993/94, First Round |
| 17.08.1993 | | Sunderland | – | Chester City | | 3:1 (0:1) |
| Sunderland |
Football League Cup 1992/93, First Round |
| 25.08.1992 | | Chester City | – | Stockport County | | 1:2 (0:1) |
| Chester |
Football League Cup 1991/92, Second round |
| 08.10.1991 | | Chester City | – | Manchester City | | 0:3 (0:1) |
| Macclesfield |
Football League Cup 1991/92, Second round |
| 25.09.1991 | | Manchester City | – | Chester City | | 3:1 (0:0) |
| Manchester |
Football League Cup 1991/92, First Round |
| 28.08.1991 | | Lincoln City | – | Chester City | | 4:3 aet |
| Lincoln |
Football League Cup 1990/91, Second round |
| 09.10.1990 | | Arsenal | – | Chester City | | 5:0 |
| London |
Football League Cup 1990/91, Second round |
| 25.09.1990 | | Chester City | – | Arsenal | | 0:1 |
| Macclesfield |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | Preston North End | – | Chester City | | 2:0 |
| Preston |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | Chester City | – | Crewe Alexandra | | 0:2 |
| Chester |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Crewe Alexandra | – | Chester City | | 4:0 |
| Crewe |
Football League Cup 1988/89, Second round |
| 12.10.1988 | | Chester City | – | Nottingham Forest | | 0:4 |
| Chester |
Football League Cup 1988/89, Second round |
| 28.09.1988 | | Nottingham Forest | – | Chester City | | 6:0 |
| Nottingham |
Football League Cup 1988/89, First Round |
| 30.08.1988 | | Bolton Wanderers | – | Chester City | | 1:0 |
| Bolton |
Football League Cup 1987/88, First Round |
| 18.08.1987 | | Blackpool | – | Chester City | | 2:0 |
| Blackpool |
Football League Cup 1986/87, First Round |
| 03.09.1986 | | Chester City | – | Derby County | | 1:2 |
| Chester |
Football League Cup 1985/86, Second round |
| 09.10.1985 | | Coventry City | – | Chester City | | 7:2 |
| |
Football League Cup 1985/86, Second round |
| 25.09.1985 | | Chester City | – | Coventry City | | 1:2 |
| |
Football League Cup 1984/85, First Round |
| 05.09.1984 | | Chester City | – | Blackpool | | 0:3 |
| |
Football League Cup 1984/85, First Round |
| 28.08.1984 | | Blackpool | – | Chester City | | 1:0 |
| |
Football League Cup 1983/84, Second round |
| 26.10.1983 | | Chester City | – | Leeds United | | 1:4 |
| |
Football League Cup 1983/84, First Round |
| 30.08.1983 | | Bolton Wanderers | – | Chester City | | 3:0 |
| |
Football League Cup 1982/83, First Round |
| 14.09.1982 | | Blackpool | – | Chester City | | 5:1 |
| |
Football League Cup 1982/83, First Round |
| 01.09.1982 | | Chester City | – | Blackpool | | 1:2 |
| |
Football League Cup 1981/82, First Round |
| 15.09.1981 | | Plymouth Argyle | – | Chester City | | 1:0 |
| |
Football League Cup 1980/81, First Round |
| 11.08.1980 | | Stockport County | – | Chester City | | 1:0 |
| |
Football League Cup 1979/80, Second round |
| 28.08.1979 | | Swindon Town | – | Chester City | | 1:0 |
| |
Football League Cup 1978/79, Third round |
| 04.10.1978 | | Chester City | – | Norwich City | | 0:2 |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Burnley | – | Chester | | 2:0 |
| |
Football League Cup 1976/77, Second round |
| 31.08.1976 | | Chester | – | Swansea City | | 2:3 |
| |
Football League Cup 1976/77, First Round |
| 18.08.1976 | | Hereford United | – | Chester | | 4:3 |
| |
Football League Cup 1975/76, First Round |
| 20.08.1975 | | Wrexham | – | Chester City | | 3:0 |
| |
Football League Cup 1974/75, Semifinals |
| 22.01.1975 | | Aston Villa | – | Chester City | | 3:2 (2:1) |
| Birmingham |
Football League Cup 1973/74, First Round |
| 29.08.1973 | | Chester City | – | Wrexham | | 0:2 |
| |
Football League Cup 1972/73, Second round |
| 20.09.1972 | | Southampton | – | Chester City | | 2:0 * |
| |
Football League Cup 1971/72, First Round |
| 25.08.1971 | | Chester | – | Tranmere Rovers | | 1:3 * |
| |
Football League Cup 1970/71, Second round |
| 16.09.1970 | | Chester | – | Norwich City | | 1:2 * |
| |
Football League Cup 1969/70, First Round |
| 13.08.1969 | | Chester | – | Aston Villa | | 1:2 (0:1) |
| Chester |
Football League Cup 1968/69, First Round |
| 28.08.1968 | | Chester | – | Tranmere Rovers | | 1:2 * |
| |
Football League Cup 1967/68, First Round |
| 22.08.1967 | | Port Vale | – | Chester | | 3:0 |
| |
Football League Cup 1966/67, First Round |
| 24.08.1966 | | Chester | – | Tranmere Rovers | | 2:5 |
| |
Football League Cup 1965/66, First Round |
| 01.09.1965 | | Wrexham | – | Chester | | 5:2 |
| |
Football League Cup 1964/65, Third round |
| 21.10.1964 | | Norwich City | – | Chester | | 5:3 |
| |
Football League Cup 1963/64, First Round |
| 18.09.1963 | | Chester | – | Rochdale | | 2:5 * |
| |
Football League Cup 1962/63, Third round |
| 17.10.1962 | | Leyton Orient | – | Chester | | 9:2 |
| |
Football League Cup 1961/62, First Round |
| 13.09.1961 | | Reading | – | Chester | | 4:2 |
| |
Football League Cup 1960/61, First Round |
| 17.10.1960 | | Leyton Orient | – | Chester | | 1:0 * |
| |
