FA Cup 2009/10, Fourth Qualifying Round |
 | 24.10.2009 |  | Barrow | – | Chester City | | 1:1 |
| |
FA Cup 2006/07, Third Round Proper |
| 06.01.2007 | | Chester City | – | Ipswich Town | | 0:0 |
| Chester |
FA Cup 2006/07, Second Round Proper |
| 02.12.2006 | | Bury | – | Chester City | | 2:2 (0:0) |
| Bury |
FA Cup 2005/06, Third Round Proper |
| 07.01.2006 | | Cheltenham Town | – | Chester City | | 2:2 (0:0) |
| Cheltenham |
FA Cup 2000/01, First Round Proper |
| 18.11.2000 | | Chester City | – | Plymouth Argyle | | 1:1 (0:0) |
| Chester |
FA Cup 1999/00, First Round Proper |
| 30.10.1999 | | Whyteleafe | – | Chester City | | 0:0 |
| |
FA Cup 1993/94, First Round Proper |
| 13.11.1993 | | Bradford City | – | Chester City | | 0:0 |
| Bradford |
FA Cup 1992/93, First Round Proper |
| 14.11.1992 | | Chester City | – | Altrincham | | 1:1 (1:0) |
| Chester |
FA Cup 1990/91, Second Round Proper |
| 12.12.1990 | | Leek Town | – | Chester City | | 1:1 |
| Leek |
FA Cup 1990/91, First Round Proper |
| 17.11.1990 | | Chester City | – | Doncaster Rovers | | 2:2 |
| Macclesfield |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Macclesfield Town | – | Chester City | | 1:1 |
| Macclesfield |
FA Cup 1986/87, Fourth Round Proper |
| 31.01.1987 | | Chester City | – | Sheffield Wednesday | | 1:1 |
| Chester |
FA Cup 1986/87, First Round Proper |
| 18.11.1986 | | Rotherham United | – | Chester City | | 1:1 aet
(0:0, 1:1) * |
| Rotherham |
FA Cup 1986/87, First Round Proper |
| 15.11.1986 | | Chester City | – | Rotherham United | | 1:1 (0:0) |
| Chester |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Chester | – | Northwich Victoria | | 1:1 |
| |
FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Chester | – | Runcorn | | 1:1 |
| |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Darlington | – | Chester | | 0:0 |
| |
FA Cup 1972/73, First Round Proper |
| 18.11.1972 | | Bolton Wanderers | – | Chester | | 1:1 |
| |
FA Cup 1971/72, First Round Proper |
| 20.11.1971 | | Chester | – | Mansfield Town | | 1:1 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Preston North End | – | Chester | | 1:1 |
| |
FA Cup 1969/70, Second Round Proper |
| 06.12.1969 | | Chester | – | Doncaster Rovers | | 1:1 (0:1) |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Halifax Town | – | Chester | | 3:3 (1:2) |
| |
FA Cup 1968/69, Second Round Proper |
| 07.12.1968 | | Chester | – | Lincoln City | | 1:1 |
| |
FA Cup 1958/59, Second Round Proper |
| 06.12.1958 | | Chester | – | Bury | | 1:1 |
| |
FA Cup 1957/58, Second Round Proper |
| 07.12.1957 | | Chester | – | Bradford City | | 3:3 |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | Chester | – | Barrow | | 0:0 |
| |
FA Cup 1951/52, Third Round Proper |
| 12.01.1952 | | Chelsea | – | Chester | | 2:2 |
| |
FA Cup 1946/47, Fourth Round Proper |
| 25.01.1947 | | Chester | – | Stoke City | | 0:0 |
| |
FA Cup 1938/39, Fourth Round Proper |
| 25.01.1939 | | Chester | – | Sheffield Wednesday | | 1:1 aet * |
| |
FA Cup 1938/39, Fourth Round Proper |
| 21.01.1939 | | Sheffield Wednesday | – | Chester | | 1:1 |
| |
FA Cup 1938/39, Second Round Proper |
| 10.12.1938 | | Chester | – | Hull City | | 2:2 |
| |
FA Cup 1935/36, Second Round Proper |
| 14.12.1935 | | Chester | – | Reading | | 3:3 |
| |
FA Cup 1932/33, Fourth Round Proper |
| 28.01.1933 | | Chester | – | Halifax Town | | 0:0 |
| |
