Football League Cup 2024/25, First Round |
| 13.08.2024 | | Derby County | | Chesterfield | | 2:1 (1:1) |
| Derby |
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 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, 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 2006/07, First Round |
| 23.08.2006 | | Chesterfield | | Wolverhampton Wanderers | | 0:0 aet, pen. 4:3 |
| Chesterfield |
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 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 2002/03, First Round |
| 10.09.2002 | | Grimsby Town | | Chesterfield | | 0:1 (0:0) |
| Cleethorpes |
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 2000/01, Second round |
| 19.09.2000 | | Chesterfield | | Fulham | | 1:0 (0:0) |
| 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 2000/01, First Round |
| 22.08.2000 | | Port Vale | | Chesterfield | | 1:2 (1:2) |
| Stoke-on-Trent |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Middlesbrough | | Chesterfield | | 2:1 (1:0) |
| Middlesbrough |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Chesterfield | | Middlesbrough | | 0:0 |
| Chesterfield |
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, 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 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, 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 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 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 |
| 27.09.1994 | | Wolverhampton Wanderers | | Chesterfield | | 1:1 (1:0) |
| Wolverhampton |
Football League Cup 1994/95, Second round |
| 20.09.1994 | | Chesterfield | | Wolverhampton Wanderers | | 1:3 (1:0) |
| Chesterfield |
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, 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 1993/94, First Round |
| 24.08.1993 | | Carlisle United | | Chesterfield | | 1:1 (1:1) |
| Carlisle |
Football League Cup 1993/94, First Round |
| 17.08.1993 | | Chesterfield | | Carlisle United | | 3:1 (1:1) |
| Chesterfield |
Football League Cup 1992/93, Second round |
| 06.10.1992 | | Chesterfield | | Liverpool | | 1:4 (1:3) |
| Chesterfield |
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 1992/93, First Round |
| 18.08.1992 | | Chesterfield | | York City | | 2:0 (0:0) |
| 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 |
| 11.09.1990 | | Hartlepool United | | Chesterfield | | 2:2 |
| Hartlepool |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | Chesterfield | | Hartlepool United | | 1:2 |
| Chesterfield |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | Chesterfield | | Birmingham City | | 1:1 |
| Chesterfield |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Birmingham City | | Chesterfield | | 2:1 |
| Birmingham |
Football League Cup 1988/89, First Round |
| 06.09.1988 | | Chesterfield | | Port Vale | | 1:1 |
| Chesterfield |
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 1987/88, First Round |
| 18.08.1987 | | Chesterfield | | Peterborough United | | 2:1 |
| Chesterfield |
Football League Cup 1986/87, First Round |
| 02.09.1986 | | Wrexham | | Chesterfield | | 2:2 |
| Wrexham |
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 1985/86, First Round |
| 21.08.1985 | | Bradford City | | Chesterfield | | 2:2 |
| |
Football League Cup 1984/85, First Round |
| 04.09.1984 | | Chesterfield | | Halifax Town | | 1:2 |
| |
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 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 1983/84, First Round |
| 30.08.1983 | | Middlesbrough | | Chesterfield | | 0:1 |
| |
Football League Cup 1982/83, First Round |
| 15.09.1982 | | Hartlepool United | | Chesterfield | | 2:0 aet |
| |
Football League Cup 1982/83, First Round |
| 31.08.1982 | | Chesterfield | | Hartlepool United | | 2:1 |
| |
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 1980/81, Second round |
| 03.09.1980 | | Oxford United | | Chesterfield | | 3:0 |
| |
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, Third round |
| 25.09.1979 | | Liverpool | | Chesterfield | | 3:1 |
| Liverpool |
Football League Cup 1979/80, Second round |
| 04.09.1979 | | Shrewsbury Town | | Chesterfield | | 0:0 |
| |
Football League Cup 1979/80, Second round |
| 28.08.1979 | | Chesterfield | | Shrewsbury Town | | 3:0 |
| |
Football League Cup 1979/80, First Round |
| 14.08.1979 | | Hartlepool United | | Chesterfield | | 2:1 |
| |
Football League Cup 1979/80, First Round |
| 11.08.1979 | | Chesterfield | | Hartlepool United | | 5:1 |
| |
Football League Cup 1978/79, Third round |
| 04.10.1978 | | Chesterfield | | Charlton Athletic | | 4:5 |
| |
Football League Cup 1978/79, Second round |
| 29.08.1978 | | Orient | | Chesterfield | | 1:2 |
| |
Football League Cup 1978/79, First Round |
| 16.08.1978 | | Chesterfield | | Barnsley | | 0:0 |
| |
Football League Cup 1978/79, First Round |
| 12.08.1978 | | Barnsley | | Chesterfield | | 1:2 |
| |
Football League Cup 1977/78, Second round |
| 31.08.1977 | | Chesterfield | | Manchester City | | 0:1 |
| |
Football League Cup 1977/78, First Round |
| 23.08.1977 | | Barnsley | | Chesterfield | | 0:2 aet * |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | Barnsley | | Chesterfield | | 3:0 |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Chesterfield | | Barnsley | | 4:1 |
| |
Football League Cup 1976/77, First Round |
| 17.08.1976 | | Rotherham United | | Chesterfield | | 3:0 |
| |
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 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 1974/75, First Round |
| 21.08.1974 | | Chesterfield | | Grimsby Town | | 3:0 |
| |
Football League Cup 1973/74, Third round |
| 30.10.1973 | | Southampton | | Chesterfield | | 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 1973/74, First Round |
| 29.08.1973 | | Chesterfield | | Mansfield Town | | 1:1 |
| |
Football League Cup 1972/73, Third round |
| 03.10.1972 | | Millwall | | Chesterfield | | 2:0 |
| |
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 1972/73, First Round |
| 15.08.1972 | | Scunthorpe United | | Chesterfield | | 0:0 |
| |
Football League Cup 1971/72, Second round |
| 08.09.1971 | | Chesterfield | | Aston Villa | | 2:3 (1:2) |
| Chesterfield |
Football League Cup 1971/72, First Round |
| 23.08.1971 | | Mansfield Town | | Chesterfield | | 0:5 * |
| |
Football League Cup 1971/72, First Round |
| 18.08.1971 | | Chesterfield | | Mansfield Town | | 0:0 |
| |
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 1969/70, First Round |
| 13.08.1969 | | Bradford City | | Chesterfield | | 1:1 |
| |
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 1966/67, First Round |
| 24.08.1966 | | Chesterfield | | Scunthorpe United | | 2:1 |
| |
Football League Cup 1965/66, Third round |
| 20.10.1965 | | Stoke City | | Chesterfield | | 2:1 * |
| |
Football League Cup 1965/66, Third round |
| 13.10.1965 | | Chesterfield | | Stoke City | | 2:2 |
| |
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 1965/66, First Round |
| 01.09.1965 | | Notts County | | Chesterfield | | 0:0 |
| |
Football League Cup 1964/65, Fourth Round |
| 04.11.1964 | | Northampton Town | | Chesterfield | | 4:1 |
| |
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 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 |
| |
Football League Cup 1960/61, Second round |
| 14.11.1960 | | Leyton Orient | | Chesterfield | | 0:1 |
| |