FA Cup 2022/23, Third Round Proper |
 | 07.01.2023 |  | Chesterfield | – | West Bromwich Albion | | 3:3 (3:2) |
| Chesterfield |
FA Cup 2020/21, Fourth Qualifying Round |
| 24.10.2020 | | Stockport County | – | Chesterfield | | 1:1,
pen. 6:7 |
| Stockport |
FA Cup 2019/20, Fourth Qualifying Round |
| 19.10.2019 | | Chesterfield | – | Wrexham |  | 1:1 (1:0) |
| Chesterfield |
FA Cup 2018/19, First Round Proper |
| 10.11.2018 | | Chesterfield | – | Billericay Town | | 1:1 (1:0) |
| Chesterfield |
FA Cup 2015/16, Second Round Proper |
| 15.12.2015 | | Walsall | – | Chesterfield | | 0:0 aet,
pen. 5:3 * |
| Walsall |
FA Cup 2015/16, Second Round Proper |
| 05.12.2015 | | Chesterfield | – | Walsall | | 1:1 (0:1) |
| Chesterfield |
FA Cup 2014/15, Third Round Proper |
| 06.01.2015 | | Scunthorpe United | – | Chesterfield | | 2:2 (2:0) |
| Scunthorpe |
FA Cup 2008/09, Second Round Proper |
| 09.12.2008 | | Chesterfield | – | Droylsden | | 2:2 (1:0) * |
| Chesterfield |
FA Cup 2005/06, First Round Proper |
| 05.11.2005 | | Leyton Orient | – | Chesterfield | | 0:0 |
| London |
FA Cup 2001/02, Second Round Proper |
| 08.12.2001 | | Chesterfield | – | Southend United | | 1:1 (0:0) |
| Chesterfield |
FA Cup 1997/98, Second Round Proper |
| 06.12.1997 | | Grimsby Town | – | Chesterfield | | 2:2 (2:0) |
| Cleethorpes |
FA Cup 1996/97, Semi Final |
| 13.04.1997 | | Middlesbrough | – | Chesterfield | | 3:3 aet
(0:0, 2:2) |
| Manchester |
FA Cup 1994/95, First Round Proper |
| 12.11.1994 | | Chesterfield | – | Scarborough | | 0:0 |
| Chesterfield |
FA Cup 1992/93, First Round Proper |
| 25.11.1992 | | Chesterfield | – | Macclesfield Town | | 2:2 aet,
pen. 2:3 * |
| Chesterfield |
FA Cup 1992/93, First Round Proper |
| 14.11.1992 | | Macclesfield Town | – | Chesterfield | | 0:0 |
| Macclesfield |
FA Cup 1988/89, First Round Proper |
| 19.11.1988 | | Bolton Wanderers | – | Chesterfield | | 0:0 |
| Bolton |
FA Cup 1987/88, First Round Proper |
| 15.11.1987 | | Notts County | – | Chesterfield | | 3:3 (1:0) |
| Nottingham |
FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Tranmere Rovers | – | Chesterfield | | 2:2 |
| |
FA Cup 1983/84, Second Round Proper |
| 10.12.1983 | | Chesterfield | – | Burnley | | 2:2 |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Chesterfield | – | Peterborough United | | 2:2 |
| |
FA Cup 1980/81, Third Round Proper |
| 03.01.1981 | | Peterborough United | – | Chesterfield | | 1:1 |
| |
FA Cup 1980/81, Second Round Proper |
| 13.12.1980 | | Sheffield United | – | Chesterfield | | 1:1 |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Wigan Athletic | – | Chesterfield | | 2:2 |
| |
FA Cup 1979/80, First Round Proper |
| 24.11.1979 | | Grimsby Town | – | Chesterfield | | 1:1 |
| |
FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Darlington | – | Chesterfield | | 1:1 |
| |
FA Cup 1976/77, Second Round Proper |
| 14.12.1976 | | Walsall | – | Chesterfield | | 0:0 aet * |
| Walsall |
FA Cup 1976/77, Second Round Proper |
| 11.12.1976 | | Chesterfield | – | Walsall | | 1:1 |
| Chesterfield |
FA Cup 1973/74, First Round Proper |
| 24.11.1973 | | Chesterfield | – | Barnsley | | 0:0 |
| |
FA Cup 1972/73, Second Round Proper |
| 09.12.1972 | | Grimsby Town | – | Chesterfield | | 2:2 |
| |
FA Cup 1971/72, Second Round Proper |
| 11.12.1971 | | Barnsley | – | Chesterfield | | 0:0 |
| |
FA Cup 1970/71, Second Round Proper |
| 12.12.1970 | | Chesterfield | – | Workington | | 0:0 |
| |
FA Cup 1963/64, Second Round Proper |
| 07.12.1963 | | Netherfield | – | Chesterfield | | 1:1 |
| |
FA Cup 1961/62, Second Round Proper |
| 25.11.1961 | | Chesterfield | – | Oldham Athletic | | 2:2 |
| |
FA Cup 1960/61, Third Round Proper |
| 07.01.1961 | | Chesterfield | – | Blackburn Rovers | | 0:0 |
| |
FA Cup 1960/61, Second Round Proper |
| 26.11.1960 | | Chesterfield | – | Oldham Athletic | | 4:4 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Chesterfield | – | Doncaster Rovers | | 3:3 |
| |
FA Cup 1958/59, Second Round Proper |
| 06.12.1958 | | Carlisle United | – | Chesterfield | | 0:0 |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | South Shields | – | Chesterfield | | 2:2 |
| |
FA Cup 1953/54, Fourth Round Proper |
| 30.01.1954 | | Sheffield Wednesday | – | Chesterfield | | 0:0 |
| |
FA Cup 1952/53, Second Round Proper |
| 06.12.1952 | | Shrewsbury Town | – | Chesterfield | | 0:0 |
| |
FA Cup 1949/50, Fifth Round Proper |
| 11.02.1950 | | Chesterfield | – | Chelsea | | 1:1 |
| |
FA Cup 1945/46, Third Round Proper |
| 05.01.1946 | | Chesterfield | – | York City | | 1:1 |
| |
FA Cup 1938/39, Third Round Proper |
| 11.01.1939 | | Chesterfield | – | Southend United | | 1:1 |
| |
FA Cup 1937/38, Fifth Round Proper |
| 12.02.1938 | | Chesterfield | – | Tottenham Hotspur | | 2:2 |
| |
FA Cup 1937/38, Third Round Proper |
| 12.01.1938 | | Chesterfield | – | Bradford City | | 1:1 aet * |
| |
FA Cup 1937/38, Third Round Proper |
| 08.01.1938 | | Bradford City | – | Chesterfield | | 1:1 |
| |
FA Cup 1935/36, Second Round Proper |
| 14.12.1935 | | Chesterfield | – | Walsall | | 0:0 |
| |
FA Cup 1933/34, Third Round Proper |
| 13.01.1934 | | Chesterfield | – | Aston Villa | | 2:2 |
| |
FA Cup 1932/33, Third Round Proper |
| 14.01.1933 | | Sheffield Wednesday | – | Chesterfield | | 2:2 |
| |
FA Cup 1929/30, Third Round Proper |
| 11.01.1930 | | Chesterfield | – | Middlesbrough | | 1:1 |
| |
FA Cup 1929/30, First Round Proper |
| 30.11.1929 | | Southport | – | Chesterfield | | 0:0 |
| |
FA Cup 1909/10, First Round Proper |
| 15.01.1910 | | Chesterfield | – | Fulham | | 0:0 |
| |
FA Cup 1906/07, First Round Proper |
| 16.01.1907 | | Chesterfield | – | Derby County | | 1:1 aet * |
| |
FA Cup 1906/07, First Round Proper |
| 12.01.1907 | | Derby County | – | Chesterfield | | 1:1 |
| |
FA Cup 1905/06, First Round Proper |
| 13.01.1906 | | Clapton Orient | – | Chesterfield | | 0:0 |
| |
FA Cup 1904/05, Intermediate Round |
| 14.01.1905 | | Portsmouth | – | Chesterfield | | 0:0 |
| |
FA Cup 1900/01, First Round Proper |
| 09.02.1901 | | Kettering | – | Chesterfield | | 1:1 |
| |
