| Season |
Competition |
Round Reached |
Date |
Home |
|
Away |
| 2011/2012 | F.A. Cup | 1st Round | Sat 12 Nov | Chesterfield | 1 - 3 | Torquay Utd. |
| League Cup | 1st Round | Tue 09 Aug | Rochdale | 3 - 2 | Chesterfield |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern Section Final | Mon 30 Jan | Oldham Ath. | 0 - 1 | Chesterfield |
| Chesterfield won 3-1 on aggregate |
| 2010/2011 | F.A. Cup | 2nd Round | Sat 27 Nov | Burton Albion | 3 - 1 | Chesterfield |
| League Cup | 1st Round | Tue 10 Aug | Chesterfield | 1 - 2 | Middlesbrough |
| (Associate Members) | Northern Section 2nd Round | Wed 06 Oct | Sheff. Wed. | 2 - 2 | Chesterfield |
| Sheffield Wednesday won 8-7 on penalties |
| 2009/2010 | F.A. Cup | 1st Round | Sat 07 Nov | Chesterfield | 1 - 3 | Bournemouth |
| League Cup | 1st Round | Tue 11 Aug | Scunthorpe U. | 2 - 1 | Chesterfield |
| (Associate Members) | Northern Section Quarter-Final | Tue 10 Nov | Chesterfield | 1 - 3 | Carlisle Utd. |
| 2008/2009 | F.A. Cup | 3rd Round | Sat 03 Jan | Ipswich Town | 3 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 12 Aug | Preston N.E. | 2 - 0 | Chesterfield |
| (Associate Members) | Northern Section 1st Round | Wed 03 Sep | Chesterfield | 2 - 2 | Grimsby Town |
| no extra time, Grimsby Town won 4-1 on penalties |
| 2007/2008 | F.A. Cup | 1st Round | Sat 10 Nov | Chesterfield | 1 - 2 | Tranmere Rvs. |
| League Cup | 1st Round | Tue 14 Aug | Sheff. Utd. | 3 - 1 | Chesterfield |
| (Associate Members) | Northern Section 1st Round | Tue 04 Sep | Chesterfield | 1 - 3 | Hartlepool U. |
| 2006/2007 | F.A. Cup | 1st Round | Sat 11 Nov | Chesterfield | 0 - 1 | Basingstoke T. |
| League Cup | 4th Round | Tue 07 Nov | Chesterfield | 3 - 3 | Charlton Ath. |
| after extra time, 90 minutes 2-2, Charlton Athletic won 4-3 on penalties |
| (Associate Members) | Northern Section Semi-Final | Wed 10 Jan | Chesterfield | 2 - 4 | Crewe Alex. |
| 2005/2006 | F.A. Cup | 1st Round Replay | Wed 16 Nov | Chesterfield | 1 - 2 | Leyton Orient |
| League Cup | 1st Round | Wed 24 Aug | Chesterfield | 2 - 4 | Huddersfield |
| (Associate Members) | Northern Section 1st Round | Tue 18 Oct | Macclesfield | 2 - 0 | Chesterfield |
| 2004/2005 | F.A. Cup | 1st Round | Sat 13 Nov | Scunthorpe U. | 2 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 24 Aug | Rotherham U. | 2 - 1 | Chesterfield |
| (Associate Members) | Northern Section 1st Round | Tue 28 Sep | Macclesfield | 2 - 1 | Chesterfield |
| 2003/2004 | F.A. Cup | 1st Round | Sat 08 Nov | Tranmere Rvs. | 3 - 2 | Chesterfield |
| League Cup | 1st Round | Tue 12 Aug | Chesterfield | 0 - 0 | Burnley |
| after extra time, 90 minutes 0-0, Burnley won 3-2 on penalties |
| (Associate Members) | Northern Section 2nd Round | Tue 04 Nov | Lincoln City | 4 - 3 | Chesterfield |
| after extra time, 90 minutes 3-3, Lincoln City won on silver goal rule |
| 2002/2003 | F.A. Cup | 1st Round | Sat 16 Nov | Chesterfield | 1 - 2 | Morecambe |
| League Cup | 2nd Round | Tue 01 Oct | Chesterfield | 1 - 1 | West Ham Utd. |
| (Associate Members) | Northern Section 2nd Round | Tue 12 Nov | Port Vale | 1 - 1 | Chesterfield |
| after extra time, 90 minutes 1-1, Port Vale won 4-3 on penalties |
| 2001/2002 | F.A. Cup | 2nd Round Replay | Tue 18 Dec | Southend Utd. | 2 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 21 Aug | Port Vale | 2 - 1 | Chesterfield |
| (Associate Members) | Northern Section Quarter-Final | Tue 04 Dec | Chesterfield | 0 - 3 | Blackpool |
| 2000/2001 | F.A. Cup | 1st Round | Sat 18 Nov | Chesterfield | 0 - 1 | Bristol City |
| League Cup | 2nd Round | Wed 27 Sep | Fulham | 4 - 0 | Chesterfield |
| (Associate Members) | Northern Section Semi-Final | Tue 13 Feb | Lincoln City | 4 - 1 | Chesterfield |
| 1999/2000 | F.A. Cup | 1st Round | Sat 30 Oct | Chesterfield | 1 - 2 | Enfield |
| League Cup | 2nd Round | Tue 21 Sep | Middlesbrough | 2 - 1 | Chesterfield |
| Middlesbrough won 2-1 on aggregate |
| (Associate Members) | Northern Section Semi-Final | Tue 15 Feb | Chesterfield | 0 - 1 | Stoke City |
| 1998/1999 | F.A. Cup | 1st Round | Sat 14 Nov | Wycombe Wdrs. | 1 - 0 | Chesterfield |
| League Cup | 2nd Round | Tue 22 Sep | Chesterfield | 1 - 3 | Leicester City |
| Leicester City won 6-1 on aggregate |
| (Associate Members) | Northern Section Quarter-Final | Tue 19 Jan | Wrexham | 3 - 2 | Chesterfield |
| 1997/1998 | F.A. Cup | 2nd Round Replay | Tue 16 Dec | Chesterfield | 0 - 2 | Grimsby Town |
| League Cup | 2nd Round | Tue 30 Sep | Barnsley | 4 - 1 | Chesterfield |
| Barnsley won 6-2 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 09 Dec | Chesterfield | 0 - 1 | Grimsby Town |
| 1996/1997 | F.A. Cup | Semi Final Replay | Tue 22 Apr | Middlesbrough | 3 - 0 | Chesterfield |
| played at Hillsborough |
| League Cup | 1st Round | Tue 03 Sep | Chesterfield | 1 - 2 | Stockport Co. |
| Stockport County won 4-2 on aggregate |
| (Associate Members) | Northern Section 1st Round | Mon 09 Dec | Chesterfield | 0 - 2 | Preston N.E. |
| 1995/1996 | F.A. Cup | 2nd Round | Sat 02 Dec | Wrexham | 3 - 2 | Chesterfield |
| League Cup | 1st Round | Tue 05 Sep | Bury | 2 - 1 | Chesterfield |
| Bury won 3-1 on aggregate |
| (Associate Members) | Northern Section Semi-Final | Tue 30 Jan | Carlisle Utd. | 1 - 0 | Chesterfield |
| 1994/1995 | F.A. Cup | 1st Round Replay | Tue 22 Nov | Scarborough | 2 - 0 | Chesterfield |
| League Cup | 2nd Round | Tue 27 Sep | Wolves | 1 - 1 | Chesterfield |
| Wolverhampton Wanderers won 4-2 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 29 Nov | Carlisle Utd. | 1 - 0 | Chesterfield |
| 1993/1994 | F.A. Cup | 1st Round | Sat 13 Nov | Chesterfield | 0 - 1 | Rochdale |
| League Cup | 2nd Round | Tue 05 Oct | Chesterfield | 0 - 2 | West Ham Utd. |
| West Ham United won 7-1 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Six | Tue 09 Nov | Chesterfield | 1 - 2 | Lincoln City |
| 1992/1993 | F.A. Cup | 1st Round Replay | Wed 25 Nov | Chesterfield | 2 - 2 | Macclesfield |
| after extra time, 90 minutes ?-?, Macclesfield Town won 3-2 on penalties |
| League Cup | 2nd Round | Tue 06 Oct | Chesterfield | 1 - 4 | Liverpool |
| (Associate Members) | Northern Section Semi-Final | Tue 23 Feb | Stockport Co. | 2 - 1 | Chesterfield |
| 1991/1992 | F.A. Cup | 1st Round | Sat 16 Nov | Darlington | 2 - 1 | Chesterfield |
| League Cup | 1st Round | Tue 27 Aug | Chesterfield | 1 - 2 | Stoke City |
| Stoke City won 3-1 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 14 Jan | Bury | 2 - 1 | Chesterfield |
| 1990/1991 | F.A. Cup | 2nd Round | Tue 11 Dec | Chesterfield | 3 - 4 | Bolton Wdrs. |
| League Cup | 1st Round | Tue 11 Sep | Hartlepool U. | 2 - 2 | Chesterfield |
| Hartlepool United won 4-3 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Five | Tue 18 Dec | Scunthorpe U. | 3 - 1 | Chesterfield |
| 1989/1990 | F.A. Cup | 2nd Round | Sat 09 Dec | Chesterfield | 0 - 2 | Huddersfield |
| League Cup | 1st Round | Tue 29 Aug | Chesterfield | 1 - 1 | Birmingham C. |
| Birmingham City won 3-2 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Eight | Tue 12 Dec | Chesterfield | 2 - 1 | Halifax Town |
| 1988/1989 | F.A. Cup | 1st Round Replay | Mon 28 Nov | Chesterfield | 2 - 3 | Bolton Wdrs. |
| League Cup | 1st Round | Tue 06 Sep | Chesterfield | 1 - 1 | Port Vale |
| Port Vale won 4-3 on aggregate |
| (Associate Members) | Southern Section Quarter-Final | Tue 21 Feb | Chesterfield | 0 - 1 | Brentford |
| 1987/1988 | F.A. Cup | 1st Round Replay | Tue 17 Nov | Chesterfield | 0 - 1 | Notts. County |
| League Cup | 1st Round | Wed 26 Aug | Peterborough | 2 - 0 | Chesterfield |
| Peterborough United won 3-2 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 19 Jan | Halifax Town | 2 - 1 | Chesterfield |
| after extra time, 90 minutes 1-1 |
| 1986/1987 | F.A. Cup | 1st Round | Sat 15 Nov | Walsall | 2 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 02 Sep | Wrexham | 2 - 2 | Chesterfield |
| Wrexham won 4-2 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 27 Jan | Rochdale | 3 - 0 | Chesterfield |
| 1985/1986 | F.A. Cup | 1st Round Replay | Tue 19 Nov | Chesterfield | 0 - 1 | Tranmere Rvs. |
| League Cup | 1st Round | Tue 03 Sep | Chesterfield | 3 - 4 | Bradford City |
| Bradford City won 6-5 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Five | Tue 21 Jan | Chesterfield | 1 - 2 | Burnley |
| 1984/1985 | F.A. Cup | 2nd Round | Sat 08 Dec | Walsall | 1 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 04 Sep | Chesterfield | 1 - 2 | Halifax Town |
| Halifax Town won 3-2 on aggregate |
| (Associate Members) | Northern Section 2nd Round | Tue 12 Mar | York City | 1 - 0 | Chesterfield |
| 1983/1984 | F.A. Cup | 2nd Round Replay | Mon 19 Dec | Burnley | 3 - 2 | Chesterfield |
| League Cup | 2nd Round | Wed 26 Oct | Everton | 2 - 2 | Chesterfield |
| Everton won 3-2 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 21 Feb | Scunthorpe U. | 2 - 1 | Chesterfield |
| 1982/1983 | F.A. Cup | 1st Round Replay | Wed 24 Nov | Peterborough | 2 - 1 | Chesterfield |
| League Cup | 1st Round | Wed 15 Sep | Hartlepool U. | 2 - 0 | Chesterfield |
| Hartlepool United won 3-2 on aggregate |
| 1981/1982 | F.A. Cup | 2nd Round | Sat 12 Dec | Chesterfield | 0 - 1 | Huddersfield |
| League Cup | 1st Round | Tue 15 Sep | Chesterfield | 1 - 1 | Doncaster Rvs. |
| aggregate 1-1, Chesterfield won on away goals rule |
| 1980/1981 | F.A. Cup | 3rd Round Replay | Tue 06 Jan | Chesterfield | 1 - 2 | Peterborough |
| League Cup | 2nd Round | Wed 03 Sep | Oxford Utd. | 3 - 0 | Chesterfield |
| Oxford United won 4-3 on aggregate |
| 1979/1980 | F.A. Cup | 1st Round Replay | Tue 27 Nov | Chesterfield | 2 - 3 | Grimsby Town |
| League Cup | 3rd Round | Tue 25 Sep | Liverpool | 3 - 1 | Chesterfield |
| 1978/1979 | F.A. Cup | 1st Round Replay | Wed 06 Dec | Chesterfield | 0 - 1 | Darlington |
| League Cup | 3rd Round | Wed 04 Oct | Chesterfield | 4 - 5 | Charlton Ath. |
| 1977/1978 | F.A. Cup | 2nd Round | Sat 17 Dec | Blyth | 1 - 0 | Chesterfield |
| League Cup | 2nd Round | Wed 31 Aug | Chesterfield | 0 - 1 | Man. City |
| 1976/1977 | F.A. Cup | 2nd Round 2nd Replay | Tue 21 Dec | Walsall | 1 - 0 | Chesterfield |
| played at neutral ground |
| League Cup | 1st Round | Tue 17 Aug | Rotherham U. | 3 - 0 | Chesterfield |
| Rotherham United won 4-3 on aggregate |
| 1975/1976 | F.A. Cup | 1st Round | Sat 22 Nov | Bradford City | 1 - 0 | Chesterfield |
| League Cup | 1st Round | Mon 25 Aug | Chesterfield | 3 - 2 | Lincoln City |
| Lincoln City won 6-5 on aggregate |
| 1974/1975 | F.A. Cup | 3rd Round | Sat 04 Jan | Sunderland | 2 - 0 | Chesterfield |
| League Cup | 2nd Round | Tue 10 Sep | Sheff. Utd. | 3 - 1 | Chesterfield |
| 1973/1974 | F.A. Cup | 1st Round Replay | Wed 28 Nov | Barnsley | 2 - 1 | Chesterfield |
| League Cup | 3rd Round | Tue 30 Oct | Southampton | 3 - 0 | Chesterfield |
| 1972/1973 | F.A. Cup | 2nd Round Replay | Wed 13 Dec | Chesterfield | 0 - 1 | Grimsby Town |
| League Cup | 3rd Round | Tue 03 Oct | Millwall | 2 - 0 | Chesterfield |
| 1971/1972 | F.A. Cup | 3rd Round | Sat 15 Jan | Stoke City | 2 - 1 | Chesterfield |
| League Cup | 2nd Round | Wed 08 Sep | Chesterfield | 2 - 3 | Aston Villa |
| 1970/1971 | F.A. Cup | 2nd Round Replay | Wed 16 Dec | Workington | 3 - 2 | Chesterfield |
| League Cup | 1st Round | Wed 19 Aug | Mansfield Town | 6 - 2 | Chesterfield |
| 1969/1970 | F.A. Cup | 1st Round | Sat 15 Nov | Tranmere Rvs. | 3 - 0 | Chesterfield |
| League Cup | 1st Round Replay | Wed 20 Aug | Chesterfield | 0 - 1 | Bradford City |
| 1968/1969 | F.A. Cup | 3rd Round | Sat 04 Jan | Portsmouth | 3 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 13 Aug | Derby County | 3 - 0 | Chesterfield |
| 1967/1968 | F.A. Cup | 3rd Round | Sat 27 Jan | Blackpool | 2 - 1 | Chesterfield |
| League Cup | 1st Round | Wed 23 Aug | Grimsby Town | 1 - 0 | Chesterfield |
| 1966/1967 | F.A. Cup | 1st Round | Sat 26 Nov | Wrexham | 3 - 2 | Chesterfield |
| League Cup | 2nd Round | Tue 13 Sep | York City | 3 - 2 | Chesterfield |
| 1965/1966 | F.A. Cup | 1st Round | Sat 13 Nov | Chesterfield | 0 - 2 | Chester |
| League Cup | 3rd Round Replay | Wed 20 Oct | Stoke City | 2 - 1 | Chesterfield |
| 1964/1965 | F.A. Cup | 3rd Round | Sat 09 Jan | Chesterfield | 0 - 3 | Peterborough |
| League Cup | 4th Round | Wed 04 Nov | Northampton | 4 - 1 | Chesterfield |
| 1963/1964 | F.A. Cup | 3rd Round | Sat 04 Jan | Oxford Utd. | 1 - 0 | Chesterfield |
| League Cup | 1st Round | Wed 04 Sep | Chesterfield | 0 - 1 | Halifax Town |
| 1962/1963 | F.A. Cup | 2nd Round | Sat 24 Nov | Barnsley | 2 - 1 | Chesterfield |
| League Cup | 1st Round | Wed 05 Sep | Darlington | 1 - 0 | Chesterfield |
| 1961/1962 | F.A. Cup | 2nd Round Replay | Wed 29 Nov | Oldham Ath. | 4 - 2 | Chesterfield |
| after extra time, 90 minutes ?-? |
| League Cup | 1st Round | Wed 13 Sep | Chesterfield | 2 - 3 | Norwich City |
| 1960/1961 | F.A. Cup | 3rd Round Replay | Wed 11 Jan | Blackburn R. | 3 - 0 | Chesterfield |
| League Cup | 3rd Round | Wed 23 Nov | Chesterfield | 0 - 4 | Leeds Utd. |
| 1959/1960 | F.A. Cup | 1st Round | Sat 14 Nov | South Shields | 2 - 1 | Chesterfield |
| 1958/1959 | F.A. Cup | 3rd Round | Sat 10 Jan | Colchester U. | 2 - 0 | Chesterfield |
| 1957/1958 | F.A. Cup | 1st Round | Sat 16 Nov | York City | 1 - 0 | Chesterfield |
| 1956/1957 | F.A. Cup | 3rd Round | Sat 05 Jan | Burnley | 7 - 0 | Chesterfield |
| 1955/1956 | F.A. Cup | 2nd Round | Sat 10 Dec | Chesterfield | 1 - 2 | Hartlepools |
| 1954/1955 | F.A. Cup | 1st Round | Sat 20 Nov | Hartlepools | 1 - 0 | Chesterfield |
| 1953/1954 | F.A. Cup | 4th Round Replay | Wed 03 Feb | Chesterfield | 2 - 4 | Sheff. Wed. |
| 1952/1953 | F.A. Cup | 2nd Round Replay | Wed 10 Dec | Chesterfield | 2 - 4 | Shrewsbury Tn. |
| 1951/1952 | F.A. Cup | 2nd Round | Sat 15 Dec | Norwich City | 3 - 1 | Chesterfield |
| 1950/1951 | F.A. Cup | 3rd Round | Sat 06 Jan | Brighton & HA | 2 - 1 | Chesterfield |
| 1949/1950 | F.A. Cup | 5th Round Replay | Wed 15 Feb | Chelsea | 3 - 0 | Chesterfield |
| 1948/1949 | F.A. Cup | 3rd Round | Sat 08 Jan | Wolves | 6 - 0 | Chesterfield |
| 1947/1948 | F.A. Cup | 3rd Round | Sat 10 Jan | Derby County | 2 - 0 | Chesterfield |
| 1946/1947 | F.A. Cup | 4th Round | Sat 25 Jan | Middlesbrough | 2 - 1 | Chesterfield |
| 1945/1946 | F.A. Cup | 3rd Round | Wed 09 Jan | York City | 3 - 2 | Chesterfield |
| after extra time, 90 minutes ?-?, York City won 4-3 on aggregate |
| 1938/1939 | F.A. Cup | 3rd Round Replay | Mon 16 Jan | Southend Utd. | 4 - 3 | Chesterfield |
| 1937/1938 | F.A. Cup | 5th Round Replay | Wed 16 Feb | Tottenham H. | 2 - 1 | Chesterfield |
| 1936/1937 | F.A. Cup | 3rd Round | Sat 16 Jan | Chesterfield | 1 - 5 | Arsenal |
| 1935/1936 | F.A. Cup | 2nd Round Replay | Thu 19 Dec | Walsall | 2 - 1 | Chesterfield |
| 1934/1935 | F.A. Cup | 3rd Round | Sat 12 Jan | Swindon Town | 2 - 1 | Chesterfield |
| 1933/1934 | F.A. Cup | 3rd Round Replay | Wed 17 Jan | Aston Villa | 2 - 0 | Chesterfield |
| 1932/1933 | F.A. Cup | 5th Round | Sat 18 Feb | Burnley | 1 - 0 | Chesterfield |
| 1931/1932 | F.A. Cup | 4th Round | Sat 23 Jan | Chesterfield | 2 - 4 | Liverpool |
| 1930/1931 | F.A. Cup | 1st Round | Sat 29 Nov | Chesterfield | 1 - 2 | Notts. County |
| 1929/1930 | F.A. Cup | 3rd Round Replay | Wed 15 Jan | Middlesbrough | 4 - 3 | Chesterfield |
| 1928/1929 | F.A. Cup | 3rd Round | Sat 12 Jan | Chesterfield | 1 - 7 | Huddersfield |
| 1927/1928 | F.A. Cup | 1st Round | Sat 26 Nov | Darlington | 4 - 1 | Chesterfield |
| 1926/1927 | F.A. Cup | 3rd Round | Sat 08 Jan | Fulham | 4 - 3 | Chesterfield |
| 1925/1926 | F.A. Cup | 3rd Round | Sat 09 Jan | Chesterfield | 0 - 1 | Clapton Orient |
| 1913/1914 | F.A. Cup | 1st Round | Sat 10 Jan | West Ham Utd. | 8 - 1 | Chesterfield |
| 1912/1913 | F.A. Cup | 1st Round | Sat 18 Jan | Chesterfield | 1 - 4 | Nottm. Forest |
| 1910/1911 | F.A. Cup | 2nd Round | Sat 04 Feb | Chelsea | 4 - 1 | Chesterfield |
| 1909/1910 | F.A. Cup | 1st Round Replay | Wed 19 Jan | Fulham | 2 - 1 | Chesterfield |
| 1908/1909 | F.A. Cup | 1st Round | Sat 16 Jan | Chesterfield | 0 - 2 | Glossop N. E. |
| 1907/1908 | F.A. Cup | 2nd Round | Sat 01 Feb | Bristol Rvs. | 2 - 0 | Chesterfield |
| 1906/1907 | F.A. Cup | 1st Round Replay | Mon 21 Jan | Chesterfield | 0 - 4 | Derby County |
| replayed after initial abandoned game 16/01 (1-1) |
| 1905/1906 | F.A. Cup | 2nd Round | Sat 03 Feb | Everton | 3 - 0 | Chesterfield |
| 1900/1901 | F.A. Cup | 1st Round Replay | Wed 13 Feb | Chesterfield | 1 - 2 | Kettering Tn. |
| 1895/1896 | F.A. Cup | 1st Round | Sat 01 Feb | Chesterfield | 0 - 4 | Newcastle Utd. |
| 1894/1895 | F.A. Cup | 1st Round | Sat 02 Feb | Middlesbrough | 4 - 0 | Chesterfield |
