Football League Cup 2017/18, First Round |
 | 08.08.2017 |  | Sheffield Wednesday | – | Chesterfield | | 4:1 (2:1) |
| Sheffield |
Football League Cup 2016/17, First Round |
| 09.08.2016 | | Rochdale | – | Chesterfield | | 3:1 (0:1) |
| Rochdale |
Football League Cup 2015/16, First Round |
| 11.08.2015 | | Carlisle United | – | Chesterfield | | 3:1 aet
(0:0, 1:1) |
| Carlisle |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Chesterfield | – | Huddersfield Town | | 3:5 aet
(2:0, 3:3) |
| Chesterfield |
Football League Cup 2013/14, First Round |
| 07.08.2013 | | Leeds United | – | Chesterfield | | 2:1 (2:1) |
| Leeds |
Football League Cup 2012/13, First Round |
| 14.08.2012 | | Chesterfield | – | Tranmere Rovers | | 1:2 aet
(0:0) |
| Chesterfield |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Rochdale | – | Chesterfield | | 3:2 aet
(1:1, 1:1) |
| Rochdale |
Football League Cup 2010/11, First Round |
| 10.08.2010 | | Chesterfield | – | Middlesbrough | | 1:2 (0:2) |
| Chesterfield |
Football League Cup 2009/10, First Round |
| 11.08.2009 | | Scunthorpe United | – | Chesterfield | | 2:1 (1:0) |
| Scunthorpe |
Football League Cup 2008/09, First Round |
| 12.08.2008 | | Preston North End | – | Chesterfield | | 2:0 (1:0) |
| Preston |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Sheffield United | – | Chesterfield | | 3:1 (2:1) |
| Sheffield |
Football League Cup 2005/06, First Round |
| 24.08.2005 | | Chesterfield | – | Huddersfield Town | | 2:4 (1:1) |
| Chesterfield |
Football League Cup 2004/05, First Round |
| 24.08.2004 | | Rotherham United | – | Chesterfield | | 2:1 (1:1) |
| Rotherham |
Football League Cup 2001/02, First Round |
| 21.08.2001 | | Port Vale | – | Chesterfield | | 2:1 (2:1) |
| Stoke-on-Trent |
Football League Cup 2000/01, Second round |
| 27.09.2000 | | Fulham | – | Chesterfield | | 4:0 (1:0) |
| London |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Middlesbrough | – | Chesterfield | | 2:1 (1:0) |
| Middlesbrough |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Chesterfield | – | Leicester City | | 1:3 (1:0) |
| Chesterfield |
Football League Cup 1998/99, Second round |
| 16.09.1998 | | Leicester City | – | Chesterfield | | 3:0 (1:0) |
| Leicester |
Football League Cup 1997/98, Second round |
| 30.09.1997 | | Barnsley | – | Chesterfield | | 4:1 (2:0) |
| Barnsley |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Chesterfield | – | Barnsley | | 1:2 (0:0) |
| Chesterfield |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | Chesterfield | – | Stockport County | | 1:2 (0:0) |
| Chesterfield |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Stockport County | – | Chesterfield | | 2:1 (1:0) |
| Stockport |
Football League Cup 1995/96, First Round |
| 05.09.1995 | | Bury | – | Chesterfield | | 2:1 (0:1) |
| Bury |
Football League Cup 1995/96, First Round |
| 15.08.1995 | | Chesterfield | – | Bury | | 0:1 (0:0) |
| Chesterfield |
Football League Cup 1994/95, Second round |
| 20.09.1994 | | Chesterfield | – | Wolverhampton Wanderers | | 1:3 (1:0) |
| Chesterfield |
Football League Cup 1993/94, Second round |
| 05.10.1993 | | Chesterfield | – | West Ham United | | 0:2 (0:0) |
| Chesterfield |
Football League Cup 1993/94, Second round |
| 22.09.1993 | | West Ham United | – | Chesterfield | | 5:1 (3:0) |
| London |
Football League Cup 1992/93, Second round |
| 06.10.1992 | | Chesterfield | – | Liverpool | | 1:4 (1:3) |
| Chesterfield |
Football League Cup 1991/92, First Round |
| 27.08.1991 | | Chesterfield | – | Stoke City | | 1:2 (0:1) |
| Chesterfield |
Football League Cup 1991/92, First Round |
| 21.08.1991 | | Stoke City | – | Chesterfield | | 1:0 (1:0) |
| Stoke-on-Trent |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | Chesterfield | – | Hartlepool United | | 1:2 |
| Chesterfield |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Birmingham City | – | Chesterfield | | 2:1 |
| Birmingham |
Football League Cup 1988/89, First Round |
| 30.08.1988 | | Port Vale | – | Chesterfield | | 3:2 |
| Stoke-on-Trent |
Football League Cup 1987/88, First Round |
| 26.08.1987 | | Peterborough United | – | Chesterfield | | 2:0 |
| Peterborough |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Chesterfield | – | Wrexham |  | 0:2 |
| Chesterfield |
Football League Cup 1985/86, First Round |
| 03.09.1985 | | Chesterfield | – | Bradford City | | 3:4 aet |
| |
Football League Cup 1984/85, First Round |
| 04.09.1984 | | Chesterfield | – | Halifax Town | | 1:2 |
| |
Football League Cup 1983/84, Second round |
| 04.10.1983 | | Chesterfield | – | Everton | | 0:1 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Chesterfield | – | Middlesbrough | | 0:1 aet,
pen. 5:3 |
| |
Football League Cup 1982/83, First Round |
| 15.09.1982 | | Hartlepool United | – | Chesterfield | | 2:0 aet |
| |
Football League Cup 1980/81, Second round |
| 03.09.1980 | | Oxford United | – | Chesterfield | | 3:0 |
| |
Football League Cup 1979/80, Third round |
| 25.09.1979 | | Liverpool | – | Chesterfield | | 3:1 |
| Liverpool |
Football League Cup 1979/80, First Round |
| 14.08.1979 | | Hartlepool United | – | Chesterfield | | 2:1 |
| |
Football League Cup 1978/79, Third round |
| 04.10.1978 | | Chesterfield | – | Charlton Athletic | | 4:5 |
| |
Football League Cup 1977/78, Second round |
| 31.08.1977 | | Chesterfield | – | Manchester City | | 0:1 |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | Barnsley | – | Chesterfield | | 3:0 |
| |
Football League Cup 1976/77, First Round |
| 17.08.1976 | | Rotherham United | – | Chesterfield | | 3:0 |
| |
Football League Cup 1975/76, First Round |
| 20.08.1975 | | Lincoln City | – | Chesterfield | | 4:2 |
| |
Football League Cup 1974/75, Second round |
| 10.09.1974 | | Sheffield United | – | Chesterfield | | 3:1 |
| |
Football League Cup 1973/74, Third round |
| 30.10.1973 | | Southampton | – | Chesterfield | | 3:0 |
| |
Football League Cup 1972/73, Third round |
| 03.10.1972 | | Millwall | – | Chesterfield | | 2:0 |
| |
Football League Cup 1971/72, Second round |
| 08.09.1971 | | Chesterfield | – | Aston Villa | | 2:3 (1:2) |
| Chesterfield |
Football League Cup 1970/71, First Round |
| 19.08.1970 | | Mansfield Town | – | Chesterfield | | 6:2 |
| |
Football League Cup 1969/70, First Round |
| 20.08.1969 | | Chesterfield | – | Bradford City | | 0:1 * |
| |
Football League Cup 1968/69, First Round |
| 13.08.1968 | | Derby County | – | Chesterfield | | 3:0 |
| |
Football League Cup 1967/68, First Round |
| 23.08.1967 | | Grimsby Town | – | Chesterfield | | 1:0 |
| |
Football League Cup 1966/67, Second round |
| 13.09.1966 | | York City | – | Chesterfield | | 3:2 |
| |
Football League Cup 1965/66, Third round |
| 20.10.1965 | | Stoke City | – | Chesterfield | | 2:1 * |
| |
Football League Cup 1964/65, Fourth Round |
| 04.11.1964 | | Northampton Town | – | Chesterfield | | 4:1 |
| |
Football League Cup 1963/64, First Round |
| 04.09.1963 | | Chesterfield | – | Halifax Town | | 0:1 |
| |
Football League Cup 1962/63, First Round |
| 05.09.1962 | | Darlington | – | Chesterfield | | 1:0 |
| |
Football League Cup 1961/62, First Round |
| 13.09.1961 | | Chesterfield | – | Norwich City | | 2:3 |
| |
Football League Cup 1960/61, Third round |
| 23.11.1960 | | Chesterfield | – | Leeds United | | 0:4 |
| |
