FA Cup 2006/07, First Round Proper |
| 11.11.2006 | | Clevedon Town | | Chester City | | 1:4 (0:1) |
| Clevedon |
FA Cup 2005/06, Second Round Proper |
| 03.12.2005 | | Chester City | | Nottingham Forest | | 3:0 (1:0) |
| Chester |
FA Cup 2005/06, First Round Proper |
| 05.11.2005 | | Chester City | | Folkestone Invicta | | 2:1 (0:1) |
| Chester |
FA Cup 2004/05, Second Round Proper |
| 04.12.2004 | | Halifax Town | | Chester City | | 1:3 (0:1) |
| Halifax |
FA Cup 2004/05, First Round Proper |
| 13.11.2004 | | Stafford Rangers | | Chester City | | 0:2 (0:1) |
| Stafford |
FA Cup 2003/04, Fourth Qualifying Round |
| | | Blyth Spartans | | Chester City | | 0:1 (0:1) |
| |
FA Cup 2002/03, First Round Proper |
| 16.11.2002 | | Colchester United | | Chester City | | 0:1 (0:0) |
| Colchester |
FA Cup 2002/03, Fourth Qualifying Round |
| | | Radcliffe Borough | | Chester City | | 2:4 (0:0) |
| |
FA Cup 2000/01, Second Round Proper |
| 09.12.2000 | | Chester City | | Oxford United | | 3:2 (1:2) |
| Chester |
FA Cup 2000/01, First Round Proper |
| 28.11.2000 | | Plymouth Argyle | | Chester City | | 1:2 aet (0:1, 1:1) * |
| Plymouth |
FA Cup 2000/01, Fourth Qualifying Round |
| | | Easington Colliery | | Chester City | | 0:2 (0:1) |
| |
FA Cup 1999/00, Second Round Proper |
| 20.11.1999 | | Stalybridge Celtic | | Chester City | | 1:2 (1:1) |
| Stalybridge |
FA Cup 1999/00, First Round Proper |
| 09.11.1999 | | Chester City | | Whyteleafe | | 3:1 (1:1) * |
| Chester |
FA Cup 1997/98, First Round Proper |
| 15.11.1997 | | Chester City | | Winsford United | | 2:1 (0:1) |
| Chester |
FA Cup 1996/97, Second Round Proper |
| 07.12.1996 | | Chester City | | Boston United | | 1:0 (1:0) |
| Chester |
FA Cup 1996/97, First Round Proper |
| 16.11.1996 | | Chester City | | Stalybridge Celtic | | 3:0 (0:0) |
| Chester |
FA Cup 1994/95, First Round Proper |
| 12.11.1994 | | Chester City | | Witton Albion | | 2:0 (2:0) |
| Chester |
FA Cup 1993/94, Second Round Proper |
| 04.12.1993 | | Chester City | | Hull City | | 2:0 (2:0) |
| Chester |
FA Cup 1993/94, First Round Proper |
| 30.11.1993 | | Chester City | | Bradford City | | 1:0 (1:0) * |
| Chester |
FA Cup 1991/92, First Round Proper |
| 16.11.1991 | | Chester City | | Guiseley | | 1:0 |
| |
FA Cup 1990/91, Second Round Proper |
| 17.12.1990 | | Chester City | | Leek Town | | 4:0 * |
| |
FA Cup 1990/91, First Round Proper |
| 20.11.1990 | | Doncaster Rovers | | Chester City | | 1:2 * |
| Doncaster |
FA Cup 1989/90, First Round Proper |
| 21.11.1989 | | Chester City | | Macclesfield Town | | 3:2 * |
| Chester |
FA Cup 1988/89, First Round Proper |
| 19.11.1988 | | Burnley | | Chester City | | 0:2 (0:0) |
| Burnley |
FA Cup 1986/87, Third Round Proper |
| 10.01.1987 | | Wrexham | | Chester City | | 1:2 (1:0) |
| Wrexham |
FA Cup 1986/87, Second Round Proper |
| 06.12.1986 | | Chester City | | Doncaster Rovers | | 3:1 (0:0) |
| Chester |
FA Cup 1986/87, First Round Proper |
| 24.11.1986 | | Chester City | | Rotherham United | | 1:0 (0:0) * |
| Chester |
FA Cup 1979/80, Fourth Round Proper |
| 26.01.1980 | | Chester | | Millwall | | 2:0 |
| |
FA Cup 1979/80, Third Round Proper |
| 05.01.1980 | | Newcastle United | | Chester | | 0:2 |
| |
FA Cup 1979/80, Second Round Proper |
| 18.12.1979 | | Chester | | Barnsley | | 1:0 |
| |
FA Cup 1979/80, First Round Proper |
| 24.11.1979 | | Chester | | Workington | | 5:1 |
| |
FA Cup 1978/79, First Round Proper |
| 28.11.1978 | | Runcorn | | Chester | | 0:5 * |
| |
FA Cup 1977/78, First Round Proper |
| 26.11.1977 | | Chester | | Darlington | | 4:1 |
| |
FA Cup 1976/77, Fourth Round Proper |
| 29.01.1977 | | Chester | | Luton Town | | 1:0 |
| Chester |
FA Cup 1976/77, Third Round Proper |
| 08.01.1977 | | Southend United | | Chester | | 0:4 |
| Southend-on-Sea |
FA Cup 1976/77, Second Round Proper |
| 11.12.1976 | | Grimsby Town | | Chester | | 0:1 |
| Cleethorpes |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Chester | | Hartlepool | | 1:0 |
| Chester |
FA Cup 1975/76, First Round Proper |
| 26.11.1975 | | Chester | | Darlington | | 2:0 * |
| |
FA Cup 1973/74, Second Round Proper |
| 15.12.1973 | | Chester | | Huddersfield Town | | 3:2 |
| |
FA Cup 1973/74, First Round Proper |
| 24.11.1973 | | Chester | | Telford United | | 1:0 |
| |
FA Cup 1970/71, Second Round Proper |
| 12.12.1970 | | Chester | | Crewe Alexandra | | 1:0 |
| |
FA Cup 1970/71, First Round Proper |
| 25.11.1970 | | Chester | | Preston North End | | 1:0 * |
| |
FA Cup 1969/70, Third Round Proper |
| 03.01.1970 | | Chester | | Bristol City | | 2:1 (1:0) |
| |
FA Cup 1969/70, Second Round Proper |
| 09.12.1969 | | Doncaster Rovers | | Chester | | 0:2 (0:1) * |
| |
FA Cup 1969/70, First Round Proper |
| 19.11.1969 | | Chester | | Halifax Town | | 1:0 (1:0) * |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Bradford City | | Chester | | 1:2 |
| |
FA Cup 1967/68, First Round Proper |
| 09.12.1967 | | Port Vale | | Chester | | 1:2 |
| |
FA Cup 1965/66, Second Round Proper |
| 04.12.1965 | | Chester | | Wigan Athletic | | 2:1 |
| |
FA Cup 1965/66, First Round Proper |
| 13.11.1965 | | Chesterfield | | Chester | | 0:2 |
| |
FA Cup 1964/65, Second Round Proper |
| 05.12.1964 | | Barnsley | | Chester | | 2:5 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Chester | | Crewe Alexandra | | 5:0 |
| |
FA Cup 1963/64, First Round Proper |
| 16.11.1963 | | Chester | | Blyth Spartans | | 3:2 |
| |
FA Cup 1961/62, First Round Proper |
| 04.11.1961 | | Chester | | Ashington | | 4:1 |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Tranmere Rovers | | Chester | | 0:1 |
| |
FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Chester | | Boston United | | 3:2 |
| |
FA Cup 1957/58, First Round Proper |
| 16.11.1957 | | Chester | | Gateshead | | 4:3 |
| |
FA Cup 1951/52, Second Round Proper |
| 15.12.1951 | | Chester | | Leyton | | 5:2 |
| |
FA Cup 1951/52, First Round Proper |
| 24.11.1951 | | Accrington Stanley | | Chester | | 1:2 |
| |
FA Cup 1949/50, First Round Proper |
| 26.11.1949 | | Chester | | Goole Town | | 4:1 |
| |
FA Cup 1948/49, First Round Proper |
| 27.11.1948 | | Hartlepools United | | Chester | | 1:3 |
| |
FA Cup 1947/48, Third Round Proper |
| 10.01.1948 | | Crystal Palace | | Chester | | 0:1 |
| |
FA Cup 1947/48, Second Round Proper |
| 13.12.1947 | | Tranmere Rovers | | Chester | | 0:1 |
| |
FA Cup 1947/48, First Round Proper |
| 29.11.1947 | | Chester | | Bishop Auckland | | 3:1 |
| |
FA Cup 1946/47, Third Round Proper |
| 11.01.1947 | | Chester | | Plymouth Argyle | | 2:0 |
| |
FA Cup 1938/39, Third Round Proper |
| 07.01.1939 | | Chester | | Coventry City | | 1:0 |
| |
FA Cup 1938/39, Second Round Proper |
| 15.12.1938 | | Hull City | | Chester | | 0:1 * |
| |
FA Cup 1938/39, First Round Proper |
| 26.11.1938 | | Chester | | Bradford City | | 3:1 |
| |
FA Cup 1936/37, Third Round Proper |
| 16.01.1937 | | Chester | | Doncaster Rovers | | 4:0 |
| |
FA Cup 1935/36, First Round Proper |
| 30.11.1935 | | Chester | | Gateshead | | 1:0 |
| |
FA Cup 1934/35, Second Round Proper |
| 08.12.1934 | | Clapton Orient | | Chester | | 1:3 |
| |
FA Cup 1934/35, First Round Proper |
| 24.11.1934 | | Chester | | Dinnington Athletic | | 3:1 |
| |
FA Cup 1933/34, First Round Proper |
| 25.11.1933 | | Chester | | Darlington | | 6:1 |
| |
FA Cup 1932/33, Third Round Proper |
| 14.01.1933 | | Chester | | Fulham | | 5:0 |
| |
FA Cup 1932/33, Second Round Proper |
| 10.12.1932 | | Chester | | Yeovil & Petter's United | | 2:1 |
| |
FA Cup 1932/33, First Round Proper |
| 26.11.1932 | | Chester | | Rotherham United | | 4:0 |
| |
FA Cup 1931/32, First Round Proper |
| 28.11.1931 | | Chester | | Hartlepools United | | 4:1 |
| |
FA Cup 1890/91, First Round Proper |
| 17.01.1891 | | Chester | | Lincoln City | | 1:0 |
| |
FA Cup 1886/87, Second Round |
| 20.11.1886 | | Chester | | Goldenhill | | 1:0 * |
| |