FA Cup 2023/24, Third Round Proper |
| 06.01.2024 | | Watford | | Chesterfield | | 2:1 (0:1) |
| Watford |
FA Cup 2022/23, Third Round Proper |
| 17.01.2023 | | West Bromwich Albion | | Chesterfield | | 4:0 (1:0) * |
| West Bromwich |
FA Cup 2021/22, Third Round Proper |
| 08.01.2022 | | Chelsea | | Chesterfield | | 5:1 (4:0) |
| London |
FA Cup 2020/21, Fourth Qualifying Round |
| 04.11.2020 | | Stockport County | | Chesterfield | | 4:0 |
| Stockport |
FA Cup 2019/20, Fourth Qualifying Round |
| 22.10.2019 | | Wrexham | | Chesterfield | | 1:0 (1:0) * |
| Wrexham |
FA Cup 2018/19, Second Round Proper |
| 02.12.2018 | | Chesterfield | | Grimsby Town | | 0:2 (0:1) |
| Chesterfield |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Bradford City | | Chesterfield | | 2:0 (2:0) |
| Bradford |
FA Cup 2016/17, Second Round Proper |
| 03.12.2016 | | Chesterfield | | Wycombe Wanderers | | 0:5 (0:2) |
| Chesterfield |
FA Cup 2014/15, Fourth Round Proper |
| 24.01.2015 | | Derby County | | Chesterfield | | 2:0 (1:0) |
| Derby |
FA Cup 2013/14, Second Round Proper |
| 07.12.2013 | | Chesterfield | | Southend United | | 1:3 (1:2) |
| Chesterfield |
FA Cup 2012/13, Second Round Proper |
| 01.12.2012 | | Tranmere Rovers | | Chesterfield | | 2:1 (1:1) |
| Birkenhead |
FA Cup 2011/12, First Round Proper |
| 12.11.2011 | | Chesterfield | | Torquay United | | 1:3 (0:1) |
| Chesterfield |
FA Cup 2010/11, Second Round Proper |
| 27.11.2010 | | Burton Albion | | Chesterfield | | 3:1 (2:0) |
| Burton upon Trent |
FA Cup 2009/10, First Round Proper |
| 07.11.2009 | | Chesterfield | | AFC Bournemouth | | 1:3 (1:2) |
| Chesterfield |
FA Cup 2008/09, Third Round Proper |
| 03.01.2009 | | Ipswich Town | | Chesterfield | | 3:0 (0:0) |
| Ipswich |
FA Cup 2008/09, Second Round Proper |
| 23.12.2008 | | Droylsden | | Chesterfield | | 2:1 (1:1) * |
| |
FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Chesterfield | | Tranmere Rovers | | 1:2 (1:1) |
| Chesterfield |
FA Cup 2006/07, First Round Proper |
| 11.11.2006 | | Chesterfield | | Basingstoke Town | | 0:1 (0:1) |
| Chesterfield |
FA Cup 2005/06, First Round Proper |
| 16.11.2005 | | Chesterfield | | Leyton Orient | | 1:2 (1:2) * |
| Chesterfield |
FA Cup 2004/05, First Round Proper |
| 13.11.2004 | | Scunthorpe United | | Chesterfield | | 2:0 (1:0) |
| Scunthorpe |
FA Cup 2003/04, First Round Proper |
| 08.11.2003 | | Tranmere Rovers | | Chesterfield | | 3:2 (1:0) |
| Birkenhead |
FA Cup 2002/03, First Round Proper |
| 16.11.2002 | | Chesterfield | | Morecambe | | 1:2 (0:1) |
| Chesterfield |
FA Cup 2001/02, Second Round Proper |
| 18.12.2001 | | Southend United | | Chesterfield | | 2:0 (1:0) * |
| Southend-on-Sea |
FA Cup 2000/01, First Round Proper |
| 18.11.2000 | | Chesterfield | | Bristol City | | 0:1 (0:0) |
| Chesterfield |
FA Cup 1999/00, First Round Proper |
| 30.10.1999 | | Chesterfield | | Enfield | | 1:2 (0:1) |
| Chesterfield |
FA Cup 1998/99, First Round Proper |
| 14.11.1998 | | Wycombe Wanderers | | Chesterfield | | 1:0 (0:0) |
| High Wycombe |
FA Cup 1997/98, Second Round Proper |
| 16.12.1997 | | Chesterfield | | Grimsby Town | | 0:2 (0:1) * |
| Chesterfield |
FA Cup 1996/97, Semi Final |
| 22.04.1997 | | Middlesbrough | | Chesterfield | | 3:0 (1:0) * |
| Sheffield |
FA Cup 1995/96, Second Round Proper |
| 02.12.1995 | | Wrexham | | Chesterfield | | 3:2 (2:0) |
| Wrexham |
FA Cup 1994/95, First Round Proper |
| 22.11.1994 | | Scarborough | | Chesterfield | | 2:0 (1:0) * |
| Scunthorpe |
FA Cup 1993/94, First Round Proper |
| 13.11.1993 | | Chesterfield | | Rochdale | | 0:1 (0:0) |
| Chesterfield |
FA Cup 1991/92, First Round Proper |
| 16.11.1991 | | Darlington | | Chesterfield | | 2:1 |
| Darlington |
FA Cup 1990/91, Second Round Proper |
| 11.12.1990 | | Chesterfield | | Bolton Wanderers | | 3:4 |
| Chesterfield |
FA Cup 1989/90, Second Round Proper |
| 09.12.1989 | | Chesterfield | | Huddersfield Town | | 0:2 |
| Chesterfield |
FA Cup 1988/89, First Round Proper |
| 28.11.1988 | | Chesterfield | | Bolton Wanderers | | 2:3 (1:0) * |
| Chesterfield |
FA Cup 1987/88, First Round Proper |
| 17.11.1987 | | Chesterfield | | Notts County | | 0:1 (0:1) * |
| Chesterfield |
FA Cup 1986/87, First Round Proper |
| 15.11.1986 | | Walsall | | Chesterfield | | 2:0 (0:0) |
| Walsall |
FA Cup 1985/86, First Round Proper |
| 19.11.1985 | | Chesterfield | | Tranmere Rovers | | 0:1 * |
| |
FA Cup 1984/85, Second Round Proper |
| 08.12.1984 | | Walsall | | Chesterfield | | 1:0 |
| |
FA Cup 1983/84, Second Round Proper |
| 19.12.1983 | | Burnley | | Chesterfield | | 3:2 * |
| |
FA Cup 1982/83, First Round Proper |
| 24.11.1982 | | Peterborough United | | Chesterfield | | 2:1 * |
| |
FA Cup 1981/82, Second Round Proper |
| 12.12.1981 | | Chesterfield | | Huddersfield Town | | 0:1 |
| |
FA Cup 1980/81, Third Round Proper |
| 06.01.1981 | | Chesterfield | | Peterborough United | | 1:2 * |
| |
FA Cup 1979/80, First Round Proper |
| 27.11.1979 | | Chesterfield | | Grimsby Town | | 2:3 * |
| |
FA Cup 1978/79, First Round Proper |
| 06.12.1978 | | Chesterfield | | Darlington | | 0:1 * |
| |
FA Cup 1977/78, Second Round Proper |
| 17.12.1977 | | Blyth Spartans | | Chesterfield | | 1:0 |
| |
FA Cup 1976/77, Second Round Proper |
| 21.12.1976 | | Chesterfield | | Walsall | | 0:1 * |
| Chesterfield |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Bradford City | | Chesterfield | | 1:0 |
| |
FA Cup 1974/75, Third Round Proper |
| 04.01.1975 | | Sunderland | | Chesterfield | | 2:0 |
| |
FA Cup 1973/74, First Round Proper |
| 28.11.1973 | | Barnsley | | Chesterfield | | 2:1 * |
| |
FA Cup 1972/73, Second Round Proper |
| 13.12.1972 | | Chesterfield | | Grimsby Town | | 0:1 * |
| |
FA Cup 1971/72, Third Round Proper |
| 15.01.1972 | | Stoke City | | Chesterfield | | 2:1 |
| |
FA Cup 1970/71, Second Round Proper |
| 16.12.1970 | | Workington | | Chesterfield | | 3:2 * |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Tranmere Rovers | | Chesterfield | | 3:0 (1:0) |
| |
FA Cup 1968/69, Third Round Proper |
| 04.01.1969 | | Portsmouth | | Chesterfield | | 3:0 |
| |
FA Cup 1967/68, Third Round Proper |
| 27.01.1968 | | Blackpool | | Chesterfield | | 2:1 |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | Wrexham | | Chesterfield | | 3:2 |
| |
FA Cup 1965/66, First Round Proper |
| 13.11.1965 | | Chesterfield | | Chester | | 0:2 |
| |
FA Cup 1964/65, Third Round Proper |
| 09.01.1965 | | Chesterfield | | Peterborough United | | 0:3 |
| |
FA Cup 1963/64, Third Round Proper |
| 04.01.1964 | | Oxford United | | Chesterfield | | 1:0 |
| |
FA Cup 1962/63, Second Round Proper |
| 24.11.1962 | | Barnsley | | Chesterfield | | 2:1 |
| |
FA Cup 1961/62, Second Round Proper |
| 29.11.1961 | | Oldham Athletic | | Chesterfield | | 4:2 * |
| |
FA Cup 1960/61, Third Round Proper |
| 11.01.1961 | | Blackburn Rovers | | Chesterfield | | 3:0 * |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | South Shields | | Chesterfield | | 2:1 |
| |
FA Cup 1958/59, Third Round Proper |
| 10.01.1959 | | Colchester United | | Chesterfield | | 2:0 |
| |
FA Cup 1957/58, First Round Proper |
| 16.11.1957 | | York City | | Chesterfield | | 1:0 |
| |
FA Cup 1956/57, Third Round Proper |
| 05.01.1957 | | Burnley | | Chesterfield | | 7:0 |
| |
FA Cup 1955/56, Second Round Proper |
| 10.12.1955 | | Chesterfield | | Hartlepools United | | 1:2 |
| |
FA Cup 1954/55, First Round Proper |
| 20.11.1954 | | Hartlepools United | | Chesterfield | | 1:0 |
| |
FA Cup 1953/54, Fourth Round Proper |
| 03.02.1954 | | Chesterfield | | Sheffield Wednesday | | 2:4 * |
| |
FA Cup 1952/53, Second Round Proper |
| 10.12.1952 | | Chesterfield | | Shrewsbury Town | | 2:4 * |
| |
FA Cup 1951/52, Second Round Proper |
| 15.12.1951 | | Norwich City | | Chesterfield | | 3:1 |
| |
FA Cup 1950/51, Third Round Proper |
| 06.01.1951 | | Brighton & Hove Albion | | Chesterfield | | 2:1 |
| |
FA Cup 1949/50, Fifth Round Proper |
| 15.02.1950 | | Chelsea | | Chesterfield | | 3:0 * |
| |
FA Cup 1948/49, Third Round Proper |
| 08.01.1949 | | Wolverhampton Wanderers | | Chesterfield | | 6:0 |
| |
FA Cup 1947/48, Third Round Proper |
| 10.01.1948 | | Derby County | | Chesterfield | | 2:0 |
| |
FA Cup 1946/47, Fourth Round Proper |
| 25.01.1947 | | Middlesbrough | | Chesterfield | | 2:1 |
| |
FA Cup 1945/46, Third Round Proper |
| 09.01.1946 | | York City | | Chesterfield | | 3:2 |
| |
FA Cup 1938/39, Third Round Proper |
| 16.01.1939 | | Southend United | | Chesterfield | | 4:3 * |
| |
FA Cup 1937/38, Fifth Round Proper |
| 16.02.1938 | | Tottenham Hotspur | | Chesterfield | | 2:1 * |
| |
FA Cup 1936/37, Third Round Proper |
| 16.01.1937 | | Chesterfield | | Arsenal | | 1:5 |
| |
FA Cup 1935/36, Second Round Proper |
| 19.12.1935 | | Walsall | | Chesterfield | | 2:1 * |
| |
FA Cup 1934/35, Third Round Proper |
| 12.01.1935 | | Swindon Town | | Chesterfield | | 2:1 |
| |
FA Cup 1933/34, Third Round Proper |
| 17.01.1934 | | Aston Villa | | Chesterfield | | 2:0 * |
| |
FA Cup 1932/33, Fifth Round Proper |
| 18.02.1933 | | Burnley | | Chesterfield | | 1:0 |
| |
FA Cup 1931/32, Fourth Round Proper |
| 23.01.1932 | | Chesterfield | | Liverpool | | 2:4 |
| |
FA Cup 1930/31, First Round Proper |
| 29.11.1930 | | Chesterfield | | Notts County | | 1:2 |
| |
FA Cup 1929/30, Third Round Proper |
| 15.01.1930 | | Middlesbrough | | Chesterfield | | 4:3 * |
| |
FA Cup 1928/29, Third Round Proper |
| 12.01.1929 | | Chesterfield | | Huddersfield Town | | 1:7 |
| |
FA Cup 1927/28, First Round Proper |
| 26.11.1927 | | Darlington | | Chesterfield | | 4:1 |
| |
FA Cup 1926/27, Third Round Proper |
| 08.01.1927 | | Fulham | | Chesterfield | | 4:3 |
| |
FA Cup 1925/26, Third Round Proper |
| 09.01.1926 | | Chesterfield | | Clapton Orient | | 0:1 |
| |
FA Cup 1913/14, First Round Proper |
| 10.01.1914 | | West Ham United | | Chesterfield | | 8:1 |
| |
FA Cup 1912/13, First Round Proper |
| 18.01.1913 | | Chesterfield | | Nottingham Forest | | 1:4 |
| |
FA Cup 1910/11, Second Round Proper |
| 04.02.1911 | | Chelsea | | Chesterfield | | 4:1 |
| |
FA Cup 1909/10, First Round Proper |
| 19.01.1910 | | Fulham | | Chesterfield | | 2:1 * |
| |
FA Cup 1908/09, First Round Proper |
| 16.01.1909 | | Chesterfield | | Glossop | | 0:2 |
| |
FA Cup 1907/08, Second Round Proper |
| 01.02.1908 | | Bristol Rovers | | Chesterfield | | 2:0 |
| |
FA Cup 1906/07, First Round Proper |
| 21.01.1907 | | Chesterfield | | Derby County | | 0:4 * |
| |
FA Cup 1905/06, Second Round Proper |
| 03.02.1906 | | Everton | | Chesterfield | | 3:0 |
| |
FA Cup 1904/05, Intermediate Round |
| 18.01.1905 | | Portsmouth | | Chesterfield | | 2:0 * |
| |
FA Cup 1901/02, Intermediate Round |
| 14.12.1901 | | Reading | | Chesterfield | | 2:1 |
| |
FA Cup 1900/01, First Round Proper |
| 13.02.1901 | | Chesterfield | | Kettering | | 1:2 * |
| |
FA Cup 1895/96, First Round Proper |
| 01.02.1896 | | Chesterfield | | Newcastle United | | 0:4 |
| |
FA Cup 1894/95, First Round Proper |
| 02.02.1895 | | Middlesbrough | | Chesterfield | | 4:0 |
| |