Football League Cup 2006/07, Fourth Round |
 | 07.11.2006 | | Chesterfield | – | Charlton Athletic | | 3:3 aet
(1:1, 2:2),
pen. 3:4 |
| Chesterfield |
Football League Cup 2006/07, First Round |
| 23.08.2006 | | Chesterfield | – | Wolverhampton Wanderers | | 0:0 aet,
pen. 4:3 |
| Chesterfield |
Football League Cup 2003/04, First Round |
| 12.08.2003 | | Chesterfield | – | Burnley | | 0:0 aet,
pen. 2:3 |
| Chesterfield |
Football League Cup 2002/03, Second round |
| 01.10.2002 | | Chesterfield | – | West Ham United | | 1:1 aet
(0:1, 1:1),
pen. 4:5 |
| Chesterfield |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Chesterfield | – | Port Vale | | 2:2 aet
(0:0, 1:2) |
| Chesterfield |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Chesterfield | – | Middlesbrough | | 0:0 |
| Chesterfield |
Football League Cup 1994/95, Second round |
| 27.09.1994 | | Wolverhampton Wanderers | – | Chesterfield | | 1:1 (1:0) |
| Wolverhampton |
Football League Cup 1993/94, First Round |
| 24.08.1993 | | Carlisle United | – | Chesterfield | | 1:1 (1:1) |
| Carlisle |
Football League Cup 1992/93, Second round |
| 22.09.1992 | | Liverpool | – | Chesterfield | | 4:4 (0:2) |
| Liverpool |
Football League Cup 1992/93, First Round |
| 25.08.1992 | | York City | – | Chesterfield | | 0:0 |
| York |
Football League Cup 1990/91, First Round |
| 11.09.1990 | | Hartlepool United | – | Chesterfield | | 2:2 |
| Hartlepool |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | Chesterfield | – | Birmingham City | | 1:1 |
| Chesterfield |
Football League Cup 1988/89, First Round |
| 06.09.1988 | | Chesterfield | – | Port Vale | | 1:1 |
| Chesterfield |
Football League Cup 1986/87, First Round |
| 02.09.1986 | | Wrexham | – | Chesterfield | | 2:2 |
| Wrexham |
Football League Cup 1985/86, First Round |
| 21.08.1985 | | Bradford City | – | Chesterfield | | 2:2 |
| |
Football League Cup 1984/85, First Round |
| 28.08.1984 | | Halifax Town | – | Chesterfield | | 1:1 |
| |
Football League Cup 1983/84, Second round |
| 26.10.1983 | | Everton | – | Chesterfield | | 2:2 |
| Liverpool |
Football League Cup 1981/82, First Round |
| 15.09.1981 | | Chesterfield | – | Doncaster Rovers | | 1:1 aet |
| |
Football League Cup 1981/82, First Round |
| 01.09.1981 | | Doncaster Rovers | – | Chesterfield | | 0:0 |
| |
Football League Cup 1979/80, Second round |
| 04.09.1979 | | Shrewsbury Town | – | Chesterfield | | 0:0 |
| |
Football League Cup 1978/79, First Round |
| 16.08.1978 | | Chesterfield | – | Barnsley | | 0:0 |
| |
Football League Cup 1973/74, First Round |
| 29.08.1973 | | Chesterfield | – | Mansfield Town | | 1:1 |
| |
Football League Cup 1972/73, First Round |
| 15.08.1972 | | Scunthorpe United | – | Chesterfield | | 0:0 |
| |
Football League Cup 1971/72, First Round |
| 18.08.1971 | | Chesterfield | – | Mansfield Town | | 0:0 |
| |
Football League Cup 1969/70, First Round |
| 13.08.1969 | | Bradford City | – | Chesterfield | | 1:1 |
| |
Football League Cup 1965/66, Third round |
| 13.10.1965 | | Chesterfield | – | Stoke City | | 2:2 |
| |
Football League Cup 1965/66, First Round |
| 01.09.1965 | | Notts County | – | Chesterfield | | 0:0 |
| |
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