Football League Cup 2006/07, Third round |
 | 24.10.2006 |  | Chesterfield | – | West Ham United | | 2:1 (0:1) |
| Chesterfield |
Football League Cup 2006/07, Second round |
| 20.09.2006 | | Chesterfield | – | Manchester City | | 2:1 (0:1) |
| Chesterfield |
Football League Cup 2002/03, First Round |
| 10.09.2002 | | Grimsby Town | – | Chesterfield | | 0:1 (0:0) |
| Cleethorpes |
Football League Cup 2000/01, Second round |
| 19.09.2000 | | Chesterfield | – | Fulham | | 1:0 (0:0) |
| Chesterfield |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Port Vale | – | Chesterfield | | 1:2 (1:2) |
| Stoke-on-Trent |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Chesterfield | – | Rochdale Town | | 2:1 (1:1) |
| Chesterfield |
Football League Cup 1999/00, First Round |
| 10.08.1999 | | Rochdale Town | – | Chesterfield | | 1:2 (1:0) |
| Rochdale |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Chesterfield | – | Rotherham United | | 2:0 (0:0) |
| Chesterfield |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Rotherham United | – | Chesterfield | | 0:1 (0:1) |
| Rotherham |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Chesterfield | – | Wigan Athletic | | 1:0 (0:0) |
| Chesterfield |
Football League Cup 1997/98, First Round |
| 12.08.1997 | | Wigan Athletic | – | Chesterfield | | 1:2 (0:0) |
| Wigan |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | Chesterfield | – | Blackpool | | 4:2 (3:2) |
| Chesterfield |
Football League Cup 1994/95, First Round |
| 16.08.1994 | | Blackpool | – | Chesterfield | | 1:2 (0:2) |
| Blackpool |
Football League Cup 1993/94, First Round |
| 17.08.1993 | | Chesterfield | – | Carlisle United | | 3:1 (1:1) |
| Chesterfield |
Football League Cup 1992/93, First Round |
| 18.08.1992 | | Chesterfield | – | York City | | 2:0 (0:0) |
| Chesterfield |
Football League Cup 1987/88, First Round |
| 18.08.1987 | | Chesterfield | – | Peterborough United | | 2:1 |
| Chesterfield |
Football League Cup 1983/84, First Round |
| 30.08.1983 | | Middlesbrough | – | Chesterfield | | 0:1 |
| |
Football League Cup 1982/83, First Round |
| 31.08.1982 | | Chesterfield | – | Hartlepool United | | 2:1 |
| |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Chesterfield | – | Oxford United | | 3:1 |
| |
Football League Cup 1980/81, First Round |
| 12.08.1980 | | Darlington | – | Chesterfield | | 1:2 |
| |
Football League Cup 1980/81, First Round |
| 09.08.1980 | | Chesterfield | – | Darlington | | 1:0 |
| |
Football League Cup 1979/80, Second round |
| 28.08.1979 | | Chesterfield | – | Shrewsbury Town | | 3:0 |
| |
Football League Cup 1979/80, First Round |
| 11.08.1979 | | Chesterfield | – | Hartlepool United | | 5:1 |
| |
Football League Cup 1978/79, Second round |
| 29.08.1978 | | Orient | – | Chesterfield | | 1:2 |
| |
Football League Cup 1978/79, First Round |
| 12.08.1978 | | Barnsley | – | Chesterfield | | 1:2 |
| |
Football League Cup 1977/78, First Round |
| 23.08.1977 | | Barnsley | – | Chesterfield | | 0:2 aet * |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Chesterfield | – | Barnsley | | 4:1 |
| |
Football League Cup 1976/77, First Round |
| 14.08.1976 | | Chesterfield | – | Rotherham United | | 3:1 |
| |
Football League Cup 1975/76, First Round |
| 25.08.1975 | | Chesterfield | – | Lincoln City | | 3:2 |
| |
Football League Cup 1974/75, First Round |
| 21.08.1974 | | Chesterfield | – | Grimsby Town | | 3:0 |
| |
Football League Cup 1973/74, Second round |
| 10.10.1973 | | Chesterfield | – | Swindon Town | | 1:0 |
| |
Football League Cup 1973/74, First Round |
| 05.09.1973 | | Mansfield Town | – | Chesterfield | | 0:1 * |
| |
Football League Cup 1972/73, Second round |
| 06.09.1972 | | Portsmouth | – | Chesterfield | | 0:1 |
| |
Football League Cup 1972/73, First Round |
| 23.08.1972 | | Chesterfield | – | Scunthorpe United | | 5:0 * |
| |
Football League Cup 1971/72, First Round |
| 23.08.1971 | | Mansfield Town | – | Chesterfield | | 0:5 * |
| |
Football League Cup 1966/67, First Round |
| 24.08.1966 | | Chesterfield | – | Scunthorpe United | | 2:1 |
| |
Football League Cup 1965/66, Second round |
| 22.09.1965 | | Chesterfield | – | Bradford Park Avenue | | 3:0 |
| |
Football League Cup 1965/66, First Round |
| 08.09.1965 | | Chesterfield | – | Notts County | | 2:1 * |
| |
Football League Cup 1964/65, Third round |
| 14.10.1964 | | Chesterfield | – | Carlisle United | | 3:1 |
| |
Football League Cup 1964/65, Second round |
| 22.09.1964 | | Bristol Rovers | – | Chesterfield | | 0:2 |
| |
Football League Cup 1964/65, First Round |
| 02.09.1964 | | Chesterfield | – | Hartlepools United | | 3:0 |
| |
Football League Cup 1960/61, Second round |
| 14.11.1960 | | Leyton Orient | – | Chesterfield | | 0:1 |
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