FA Cup 2023/24, Second Round Proper |
 | 03.12.2023 | | Chesterfield | – | Leyton Orient | | 1:0 (1:0) |
| Chesterfield |
FA Cup 2023/24, First Round Proper |
| 05.11.2023 | | Chesterfield | – | Portsmouth | | 1:0 (1:0) |
| Chesterfield |
FA Cup 2023/24, Fourth Qualifying Round |
| 14.10.2023 | | Chesterfield | – | Kettering Town | | 5:0 (1:0) |
| Chesterfield |
FA Cup 2022/23, Second Round Proper |
| 26.11.2022 | | AFC Wimbledon | – | Chesterfield | | 0:2 (0:1) |
| London |
FA Cup 2022/23, First Round Proper |
| 05.11.2022 | | Chesterfield | – | Northampton Town | | 1:0 (1:0) |
| Chesterfield |
FA Cup 2022/23, Fourth Qualifying Round |
| 15.10.2022 | | Anstey Nomads | – | Chesterfield | | 0:3 (0:2) |
| Anstey |
FA Cup 2021/22, Second Round Proper |
| 05.12.2021 | | Salford City | – | Chesterfield | | 0:2 (0:1) |
| Salford |
FA Cup 2021/22, First Round Proper |
| 06.11.2021 | | Chesterfield | – | Southend United | | 3:1 (2:1) |
| Chesterfield |
FA Cup 2021/22, Fourth Qualifying Round |
| 16.10.2021 | | Curzon Ashton | – | Chesterfield | | 0:4 (0:2) |
| Ashton-under-Lyne |
FA Cup 2018/19, First Round Proper |
| 20.11.2018 | | Billericay Town | – | Chesterfield | | 1:3 (0:1) * |
| Billericay |
FA Cup 2018/19, Fourth Qualifying Round |
| 20.10.2018 | | AFC Fylde | – | Chesterfield | | 1:3 (1:2) |
| Warton |
FA Cup 2016/17, First Round Proper |
| 05.11.2016 | | Colchester United | – | Chesterfield | | 1:2 (0:1) |
| Colchester |
FA Cup 2015/16, First Round Proper |
| 09.11.2015 | | United of Manchester | – | Chesterfield | | 1:4 (0:2) |
| Bury |
FA Cup 2014/15, Third Round Proper |
| 13.01.2015 | | Chesterfield | – | Scunthorpe United | | 2:0 aet
(0:0) * |
| Chesterfield |
FA Cup 2014/15, Second Round Proper |
| 02.01.2015 | | Milton Keynes Dons | – | Chesterfield | | 0:1 (0:1) |
| Milton Keynes |
FA Cup 2014/15, Second Round Proper |
| 06.12.2014 | | Milton Keynes Dons | – | Chesterfield | | 0:1 (0:0) |
| Milton Keynes |
FA Cup 2014/15, First Round Proper |
| 09.11.2014 | | Braintree Town | – | Chesterfield | | 0:6 (0:3) |
| Braintree |
FA Cup 2013/14, First Round Proper |
| 09.11.2013 | | Chesterfield | – | Daventry Town | | 2:0 (0:0) |
| Chesterfield |
FA Cup 2012/13, First Round Proper |
| 03.11.2012 | | Chesterfield | – | Hartlepool United | | 6:1 (3:0) |
| Chesterfield |
FA Cup 2010/11, First Round Proper |
| 06.11.2010 | | Harrow Borough | – | Chesterfield | | 0:2 (0:0) |
| London |
FA Cup 2008/09, Second Round Proper |
| 16.12.2008 | | Droylsden | – | Chesterfield | | 0:2 * |
| |
FA Cup 2008/09, Second Round Proper |
| 29.11.2008 | | Chesterfield | – | Droylsden | | 1:0 * |
| |
FA Cup 2008/09, First Round Proper |
| 08.11.2008 | | Chesterfield | – | Mansfield Town | | 3:1 (1:0) |
| Chesterfield |
FA Cup 2001/02, First Round Proper |
| 17.11.2001 | | Stalybridge Celtic | – | Chesterfield | | 0:3 (0:2) |
| Stalybridge |
FA Cup 1997/98, First Round Proper |
| 15.11.1997 | | Chesterfield | – | Northwich Victoria | | 1:0 (1:0) |
| Chesterfield |
FA Cup 1996/97, Sixth Round Proper |
| 09.03.1997 | | Chesterfield | – | Wrexham | | 1:0 (0:0) |
| Chesterfield |
FA Cup 1996/97, Fifth Round Proper |
| 15.02.1997 | | Chesterfield | – | Nottingham Forest | | 1:0 (0:0) |
| Chesterfield |
FA Cup 1996/97, Fourth Round Proper |
| 04.02.1997 | | Bolton Wanderers | – | Chesterfield | | 2:3 (1:1) |
| Bolton |
FA Cup 1996/97, Third Round Proper |
| 14.01.1997 | | Chesterfield | – | Bristol City | | 2:0 (0:0) |
| Chesterfield |
FA Cup 1996/97, Second Round Proper |
| 07.12.1996 | | Chesterfield | – | Scarborough | | 2:0 (1:0) |
| Chesterfield |
FA Cup 1996/97, First Round Proper |
| 16.11.1996 | | Chesterfield | – | Bury | | 1:0 (1:0) |
| Chesterfield |
FA Cup 1995/96, First Round Proper |
| 11.11.1995 | | Scarborough | – | Chesterfield | | 0:2 (0:0) |
| Scarborough |
FA Cup 1990/91, First Round Proper |
| 17.11.1990 | | Chesterfield | – | Spennymoor United | | 3:2 |
| Chesterfield |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Shrewsbury Town | – | Chesterfield | | 2:3 |
| Shrewsbury |
FA Cup 1984/85, First Round Proper |
| 17.11.1984 | | Whitby Town | – | Chesterfield | | 1:3 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Chester City | – | Chesterfield | | 1:2 |
| |
FA Cup 1981/82, First Round Proper |
| 21.11.1981 | | Chesterfield | – | Preston North End | | 4:1 |
| |
FA Cup 1980/81, Second Round Proper |
| 16.12.1980 | | Chesterfield | – | Sheffield United | | 1:0 * |
| |
FA Cup 1980/81, First Round Proper |
| 25.11.1980 | | Chesterfield | – | Wigan Athletic | | 2:0 * |
| |
FA Cup 1977/78, First Round Proper |
| 26.11.1977 | | Chesterfield | – | Halifax Town | | 1:0 |
| |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Scunthorpe United | – | Chesterfield | | 1:2 |
| Scunthorpe |
FA Cup 1974/75, Second Round Proper |
| 14.12.1974 | | Chesterfield | – | Doncaster Rovers | | 1:0 |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Chesterfield | – | Boston United | | 3:1 |
| |
FA Cup 1972/73, First Round Proper |
| 18.11.1972 | | Chesterfield | – | Rhyl | | 4:2 |
| |
FA Cup 1971/72, Second Round Proper |
| 15.12.1971 | | Chesterfield | – | Barnsley | | 1:0 * |
| |
FA Cup 1971/72, First Round Proper |
| 20.11.1971 | | Chesterfield | – | Oldham Athletic | | 3:0 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Chesterfield | – | Halifax Town | | 2:0 |
| |
FA Cup 1968/69, Second Round Proper |
| 07.12.1968 | | Chesterfield | – | Wrexham | | 2:1 |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Chesterfield | – | Skelmersdale United | | 2:0 |
| |
FA Cup 1967/68, Second Round Proper |
| 06.01.1968 | | Chester | – | Chesterfield | | 0:1 |
| |
FA Cup 1967/68, First Round Proper |
| 09.12.1967 | | Chesterfield | – | Barnsley | | 2:0 |
| |
FA Cup 1964/65, Second Round Proper |
| 05.12.1964 | | Chesterfield | – | York City | | 2:1 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Chesterfield | – | South Shields | | 2:0 |
| |
FA Cup 1963/64, Second Round Proper |
| 11.12.1963 | | Chesterfield | – | Netherfield | | 4:1 * |
| |
FA Cup 1963/64, First Round Proper |
| 16.11.1963 | | Crook Town | – | Chesterfield | | 1:2 |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Chesterfield | – | Stockport County | | 4:1 |
| |
FA Cup 1961/62, First Round Proper |
| 04.11.1961 | | Doncaster Rovers | – | Chesterfield | | 0:4 |
| |
FA Cup 1960/61, Second Round Proper |
| 29.11.1960 | | Oldham Athletic | – | Chesterfield | | 0:3 * |
| |
FA Cup 1960/61, First Round Proper |
| 09.11.1960 | | Doncaster Rovers | – | Chesterfield | | 0:1 * |
| |
FA Cup 1958/59, Second Round Proper |
| 10.12.1958 | | Chesterfield | – | Carlisle United | | 1:0 * |
| |
FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Chesterfield | – | Rhyl | | 3:0 |
| |
FA Cup 1956/57, Second Round Proper |
| 08.12.1956 | | Chesterfield | – | Barrow | | 4:1 |
| |
FA Cup 1956/57, First Round Proper |
| 21.11.1956 | | Chesterfield | – | South Shields | | 4:0 * |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Chesterfield | – | Chester | | 1:0 |
| |
FA Cup 1953/54, Third Round Proper |
| 09.01.1954 | | Chesterfield | – | Bury | | 2:0 |
| |
FA Cup 1953/54, Second Round Proper |
| 12.12.1953 | | Southend United | – | Chesterfield | | 1:2 |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Gainsborough Trinity | – | Chesterfield | | 1:4 |
| |
FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Chesterfield | – | Workington | | 1:0 |
| |
FA Cup 1951/52, First Round Proper |
| 24.11.1951 | | Barrow | – | Chesterfield | | 0:2 |
| |
FA Cup 1949/50, Fourth Round Proper |
| 28.01.1950 | | Chesterfield | – | Middlesbrough | | 3:2 |
| |
FA Cup 1949/50, Third Round Proper |
| 07.01.1950 | | Chesterfield | – | Yeovil Town | | 3:1 |
| |
FA Cup 1946/47, Third Round Proper |
| 11.01.1947 | | Chesterfield | – | Sunderland | | 2:1 |
| |
FA Cup 1937/38, Fourth Round Proper |
| 22.01.1938 | | Chesterfield | – | Burnley | | 3:2 |
| |
FA Cup 1937/38, Third Round Proper |
| 17.01.1938 | | Bradford City | – | Chesterfield | | 0:2 * |
| |
FA Cup 1935/36, First Round Proper |
| 30.11.1935 | | Chesterfield | – | Southport | | 3:0 |
| |
FA Cup 1932/33, Fourth Round Proper |
| 28.01.1933 | | Darlington | – | Chesterfield | | 0:2 |
| |
FA Cup 1932/33, Third Round Proper |
| 18.01.1933 | | Chesterfield | – | Sheffield Wednesday | | 4:2 * |
| |
FA Cup 1931/32, Third Round Proper |
| 09.01.1932 | | Chesterfield | – | Nottingham Forest | | 5:2 |
| |
FA Cup 1929/30, Second Round Proper |
| 14.12.1929 | | Chesterfield | – | Port Vale | | 2:0 |
| |
FA Cup 1929/30, First Round Proper |
| 04.12.1929 | | Chesterfield | – | Southport | | 3:2 * |
| |
FA Cup 1928/29, Second Round Proper |
| 08.12.1928 | | Gainsborough Trinity | – | Chesterfield | | 2:3 |
| |
FA Cup 1928/29, First Round Proper |
| 24.11.1928 | | Chesterfield | – | Rochdale | | 3:2 |
| |
FA Cup 1926/27, Second Round Proper |
| 11.12.1926 | | Doncaster Rovers | – | Chesterfield | | 0:1 |
| |
FA Cup 1926/27, First Round Proper |
| 27.11.1926 | | Chesterfield | – | Mexborough | | 2:1 |
| |
FA Cup 1925/26, Second Round Proper |
| 12.12.1925 | | Worksop Town | – | Chesterfield | | 1:2 |
| |
FA Cup 1925/26, First Round Proper |
| 28.11.1925 | | Wath Athletic | – | Chesterfield | | 0:5 |
| |
FA Cup 1910/11, First Round Proper |
| 14.01.1911 | | Bolton Wanderers | – | Chesterfield | | 0:2 |
| |
FA Cup 1907/08, First Round Proper |
| 11.01.1908 | | Chesterfield | – | Stockton | | 4:0 |
| |
FA Cup 1905/06, First Round Proper |
| 17.01.1906 | | Chesterfield | – | Clapton Orient | | 3:0 * |
| |
FA Cup 1900/01, Intermediate Round |
| 05.01.1901 | | Chesterfield | – | Walsall | | 3:0 |
| |
Ukraine
Azerbaijan
Armenia
Moldova
Austria
England
Belgium
Bulgaria
Hungary
Germany
Netherlands
Spain
Italy
Poland
Portugal
Slovenia
Croatia
Montenegro
Czech
Scotland
Canada
China
Australia
