FA Cup 2009/10, Fourth Qualifying Round |
 | 27.10.2009 | | Chester City | – | Barrow | | 0:4 * |
| |
FA Cup 2008/09, First Round Proper |
| 08.11.2008 | | Chester City | – | Millwall | | 0:3 (0:0) |
| Chester |
FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Bradford City | – | Chester City | | 1:0 (1:0) |
| Bradford |
FA Cup 2006/07, Third Round Proper |
| 16.01.2007 | | Ipswich Town | – | Chester City | | 1:0 (0:0) * |
| Ipswich |
FA Cup 2006/07, Second Round Proper |
| 12.12.2006 | | Chester City | – | Bury | | 1:3 (1:1) * |
| Chester |
FA Cup 2005/06, Third Round Proper |
| 17.01.2006 | | Chester City | – | Cheltenham Town | | 0:1 (0:0) * |
| Chester |
FA Cup 2004/05, Third Round Proper |
| 08.01.2005 | | AFC Bournemouth | – | Chester City | | 2:1 (1:0) |
| Bournemouth |
FA Cup 2003/04, First Round Proper |
| 08.11.2003 | | Chester City | – | Gravesend & Northfleet | | 0:1 (0:1) |
| Chester |
FA Cup 2002/03, Second Round Proper |
| 07.12.2002 | | Morecambe | – | Chester City | | 3:2 (2:2) |
| Morecambe |
FA Cup 2001/02, Fourth Qualifying Round |
| | | Barrow | – | Chester City | | 1:0 (0:0) |
| |
FA Cup 2000/01, Third Round Proper |
| 06.01.2001 | | Blackburn Rovers | – | Chester City | | 2:0 (0:0) |
| Blackburn |
FA Cup 1999/00, Third Round Proper |
| 12.12.1999 | | Chester City | – | Manchester City | | 1:4 (1:1) |
| Chester |
FA Cup 1998/99, First Round Proper |
| 14.11.1998 | | Cardiff City | – | Chester City | | 6:0 (3:0) |
| Cardiff |
FA Cup 1997/98, Second Round Proper |
| 05.12.1997 | | Chester City | – | Wrexham | | 0:2 (0:2) |
| Chester |
FA Cup 1996/97, Third Round Proper |
| 04.01.1997 | | Middlesbrough | – | Chester City | | 6:0 (3:0) |
| Middlesbrough |
FA Cup 1995/96, First Round Proper |
| 11.11.1995 | | Blackpool | – | Chester City | | 2:1 (0:0) |
| Blackpool |
FA Cup 1994/95, Second Round Proper |
| 04.12.1994 | | Chester City | – | Burnley | | 1:2 (0:0) |
| Chester |
FA Cup 1993/94, Third Round Proper |
| 08.01.1994 | | Plymouth Argyle | – | Chester City | | 1:0 (0:0) |
| Plymouth |
FA Cup 1992/93, First Round Proper |
| 25.11.1992 | | Altrincham | – | Chester City | | 2:0 (0:0) * |
| Altrincham |
FA Cup 1991/92, Second Round Proper |
| 07.12.1991 | | Crewe Alexandra | – | Chester City | | 2:0 |
| Crewe |
FA Cup 1990/91, Third Round Proper |
| 05.01.1991 | | Chester City | – | Bournemouth | | 2:3 |
| |
FA Cup 1989/90, Second Round Proper |
| 09.12.1989 | | Blackpool | – | Chester City | | 3:0 |
| Blackpool |
FA Cup 1988/89, Second Round Proper |
| 10.12.1988 | | Huddersfield Town | – | Chester City | | 1:0 (0:0) |
| Huddersfield |
FA Cup 1987/88, First Round Proper |
| 14.11.1987 | | Chester City | – | Runcorn | | 0:1 (0:1) |
| Chester |
FA Cup 1986/87, Fourth Round Proper |
| 04.02.1987 | | Sheffield Wednesday | – | Chester City | | 3:1 * |
| Sheffield |
FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Bury | – | Chester City | | 2:0 |
| |
FA Cup 1984/85, First Round Proper |
| 17.11.1984 | | Darlington | – | Chester City | | 3:2 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Chester City | – | Chesterfield | | 1:2 |
| |
FA Cup 1982/83, First Round Proper |
| 22.11.1982 | | Northwich Victoria | – | Chester | | 3:1 * |
| |
FA Cup 1981/82, First Round Proper |
| 21.11.1981 | | Penrith | – | Chester | | 1:0 |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Chester | – | Barnsley | | 1:2 |
| |
FA Cup 1979/80, Fifth Round Proper |
| 16.02.1980 | | Ipswich Town | – | Chester | | 2:1 |
| |
FA Cup 1978/79, Second Round Proper |
| 16.12.1978 | | Darlington | – | Chester | | 2:1 |
| |
FA Cup 1977/78, Second Round Proper |
| 17.12.1977 | | Carlisle United | – | Chester | | 3:1 |
| |
FA Cup 1976/77, Fifth Round Proper |
| 26.02.1977 | | Wolverhampton Wanderers | – | Chester | | 1:0 |
| Wolverhampton |
FA Cup 1975/76, Second Round Proper |
| 13.12.1975 | | Shrewsbury Town | – | Chester | | 3:1 |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Rotherham United | – | Chester | | 1:0 |
| |
FA Cup 1973/74, Third Round Proper |
| 05.01.1974 | | Aston Villa | – | Chester | | 3:1 |
| |
FA Cup 1972/73, First Round Proper |
| 22.11.1972 | | Chester | – | Bolton Wanderers | | 0:1 * |
| |
FA Cup 1971/72, First Round Proper |
| 22.11.1971 | | Mansfield Town | – | Chester | | 4:3 * |
| |
FA Cup 1970/71, Third Round Proper |
| 02.01.1971 | | Chester | – | Derby County | | 1:2 |
| |
FA Cup 1969/70, Fourth Round Proper |
| 24.01.1970 | | Swindon Town | – | Chester | | 4:2 (2:1) |
| |
FA Cup 1968/69, Second Round Proper |
| 11.12.1968 | | Lincoln City | – | Chester | | 2:1 * |
| |
FA Cup 1967/68, Second Round Proper |
| 06.01.1968 | | Chester | – | Chesterfield | | 0:1 |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | Chester | – | Middlesbrough | | 2:5 |
| |
FA Cup 1965/66, Third Round Proper |
| 22.01.1966 | | Chester | – | Newcastle United | | 1:3 |
| |
FA Cup 1964/65, Third Round Proper |
| 09.01.1965 | | Manchester United | – | Chester | | 2:1 |
| |
FA Cup 1963/64, Second Round Proper |
| 07.12.1963 | | Chester | – | Barrow | | 0:2 |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Chester | – | Tranmere Rovers | | 0:2 |
| |
FA Cup 1961/62, Second Round Proper |
| 25.11.1961 | | Chester | – | Morecambe | | 0:1 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Chester | – | Carlisle United | | 0:1 |
| |
FA Cup 1959/60, Second Round Proper |
| 05.12.1959 | | Mansfield Town | – | Chester | | 2:0 |
| |
FA Cup 1958/59, Second Round Proper |
| 09.12.1958 | | Bury | – | Chester | | 2:1 * |
| |
FA Cup 1957/58, Second Round Proper |
| 11.12.1957 | | Bradford City | – | Chester | | 3:1 * |
| |
FA Cup 1956/57, First Round Proper |
| 22.11.1956 | | Barrow | – | Chester | | 3:1 * |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Chesterfield | – | Chester | | 1:0 |
| |
FA Cup 1954/55, First Round Proper |
| 20.11.1954 | | Gateshead | – | Chester | | 6:0 |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Stockport County | – | Chester | | 4:2 |
| |
FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Chester | – | Hartlepools United | | 0:1 |
| |
FA Cup 1951/52, Third Round Proper |
| 16.01.1952 | | Chester | – | Chelsea | | 2:3 * |
| |
FA Cup 1950/51, First Round Proper |
| 25.11.1950 | | Chester | – | Bradford Park Avenue | | 1:2 |
| |
FA Cup 1949/50, Second Round Proper |
| 10.12.1949 | | Exeter City | – | Chester | | 2:0 |
| |
FA Cup 1948/49, Second Round Proper |
| 11.12.1948 | | Aldershot | – | Chester | | 1:0 |
| |
FA Cup 1947/48, Fourth Round Proper |
| 24.01.1948 | | Blackpool | – | Chester | | 4:0 |
| |
FA Cup 1946/47, Fourth Round Proper |
| 29.01.1947 | | Stoke City | – | Chester | | 3:2 * |
| |
FA Cup 1945/46, Third Round Proper |
| 09.01.1946 | | Liverpool | – | Chester | | 2:1 |
| |
FA Cup 1945/46, Third Round Proper |
| 05.01.1946 | | Chester | – | Liverpool | | 0:2 |
| |
FA Cup 1938/39, Fourth Round Proper |
| 30.01.1939 | | Sheffield Wednesday | – | Chester | | 2:0 * |
| |
FA Cup 1937/38, Third Round Proper |
| 08.01.1938 | | Leeds United | – | Chester | | 3:1 |
| |
FA Cup 1936/37, Fourth Round Proper |
| 30.01.1937 | | Coventry City | – | Chester | | 2:0 |
| |
FA Cup 1935/36, Second Round Proper |
| 18.12.1935 | | Reading | – | Chester | | 3:0 * |
| |
FA Cup 1934/35, Third Round Proper |
| 12.01.1935 | | Chester | – | Nottingham Forest | | 0:4 |
| |
FA Cup 1933/34, Second Round Proper |
| 09.12.1933 | | Southend United | – | Chester | | 2:1 |
| |
FA Cup 1932/33, Fourth Round Proper |
| 02.02.1933 | | Halifax Town | – | Chester | | 3:2 * |
| |
FA Cup 1931/32, Second Round Proper |
| 12.12.1931 | | Darwen | – | Chester | | 2:1 |
| |
FA Cup 1890/91, Second Round Proper |
| 31.01.1891 | | Blackburn Rovers | – | Chester | | 7:0 |
| |
FA Cup 1889/90, First Round Proper |
| 18.01.1890 | | Lincoln City | – | Chester | | 2:0 |
| |
FA Cup 1887/88, First Round |
| 15.10.1887 | | Chester | – | Davenham | | 2:3 |
| |
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