| RETURN TO LEAGUE LISTING | |||||||||||
| Year | Division | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 1995/1996 | English Division 3 | Gillingham | 3-1 | Chester City | 09/01/1996 | 1 | 0 | 0 | 3 | 1 | |
| English Division 3 | Chester City | 1-1 | Gillingham | 23/09/1995 | 0 | 1 | 0 | 1 | 1 | ||
| 1993/1994 | English Division 3 | Gillingham | 2-2 | Chester City | 04/04/1994 | 0 | 1 | 0 | 2 | 2 | |
| English Division 3 | Chester City | 1-0 | Gillingham | 01/03/1994 | 0 | 0 | 1 | 0 | 1 | ||
| 1988/1989 | English Division 3 (old) | Chester City | 2-0 | Gillingham | 06/05/1989 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 (old) | Gillingham | 0-2 | Chester City | 03/12/1988 | 0 | 0 | 1 | 0 | 2 | ||
| 1987/1988 | English Division 3 (old) | Chester City | 3-1 | Gillingham | 02/03/1988 | 0 | 0 | 1 | 1 | 3 | |
| English Division 3 (old) | Gillingham | 0-1 | Chester City | 29/09/1987 | 0 | 0 | 1 | 0 | 1 | ||
| 1986/1987 | English Division 3 (old) | Gillingham | 1-2 | Chester City | 14/02/1987 | 0 | 0 | 1 | 1 | 2 | |
| English Division 3 (old) | Chester City | 1-1 | Gillingham | 15/10/1986 | 0 | 1 | 0 | 1 | 1 | ||
| 1981/1982 | English Division 3 (old) | Chester City | 0-0 | Gillingham | 06/02/1982 | 0 | 1 | 0 | 0 | 0 | |
| English Division 3 (old) | Gillingham | 0-1 | Chester City | 12/09/1981 | 0 | 0 | 1 | 0 | 1 | ||
| 1980/1981 | English Division 3 (old) | Gillingham | 2-1 | Chester City | 25/04/1981 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 (old) | Chester City | 1-2 | Gillingham | 20/12/1980 | 1 | 0 | 0 | 2 | 1 | ||
| 1979/1980 | English Division 3 (old) | Chester City | 0-2 | Gillingham | 30/04/1980 | 1 | 0 | 0 | 2 | 0 | |
| English Division 3 (old) | Gillingham | 2-2 | Chester City | 15/09/1979 | 0 | 1 | 0 | 2 | 2 | ||
| 1978/1979 | English Division 3 (old) | Chester City | 1-1 | Gillingham | 21/02/1979 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 (old) | Gillingham | 1-0 | Chester City | 16/09/1978 | 1 | 0 | 0 | 1 | 0 | ||
| 1977/1978 | English Division 3 (old) | Gillingham | 1-0 | Chester City | 21/02/1978 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 (old) | Chester City | 2-2 | Gillingham | 17/09/1977 | 0 | 1 | 0 | 2 | 2 | ||
| 1976/1977 | English Division 3 (old) | Gillingham | 1-0 | Chester City | 16/04/1977 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 (old) | Chester City | 1-0 | Gillingham | 22/02/1977 | 0 | 0 | 1 | 0 | 1 | ||
| 1975/1976 | English Division 3 (old) | Gillingham | 2-0 | Chester City | 27/03/1976 | 1 | 0 | 0 | 2 | 0 | |
| English Division 3 (old) | Chester City | 2-2 | Gillingham | 06/12/1975 | 0 | 1 | 0 | 2 | 2 | ||
| 1973/1974 | English Division 4 | Gillingham | 1-0 | Chester City | 17/03/1974 | 1 | 0 | 0 | 1 | 0 | |
| English Division 4 | Chester City | 2-4 | Gillingham | 20/10/1973 | 1 | 0 | 0 | 4 | 2 | ||
| 1972/1973 | English Division 4 | Chester City | 1-0 | Gillingham | 14/04/1973 | 0 | 0 | 1 | 0 | 1 | |
| English Division 4 | Gillingham | 1-0 | Chester City | 09/12/1972 | 1 | 0 | 0 | 1 | 0 | ||
| 1971/1972 | English Division 4 | Gillingham | 1-0 | Chester City | 08/01/1972 | 1 | 0 | 0 | 1 | 0 | |
| English Division 4 | Chester City | 5-1 | Gillingham | 28/08/1971 | 0 | 0 | 1 | 1 | 5 | ||
| 1963/1964 | English Division 4 | Gillingham | 2-1 | Chester City | 07/03/1964 | 1 | 0 | 0 | 2 | 1 | |
| English Division 4 | Chester City | 1-0 | Gillingham | 26/10/1963 | 0 | 0 | 1 | 0 | 1 | ||
| 1962/1963 | English Division 4 | Chester City | 1-0 | Gillingham | 15/12/1962 | 0 | 0 | 1 | 0 | 1 | |
| English Division 4 | Gillingham | 2-1 | Chester City | 18/08/1962 | 1 | 0 | 0 | 2 | 1 | ||
| 1961/1962 | English Division 4 | Gillingham | 0-0 | Chester City | 17/03/1962 | 0 | 1 | 0 | 0 | 0 | |
| English Division 4 | Chester City | 1-1 | Gillingham | 28/10/1961 | 0 | 1 | 0 | 1 | 1 | ||
| 1960/1961 | English Division 4 | Gillingham | 3-0 | Chester City | 17/12/1960 | 1 | 0 | 0 | 3 | 0 | |
| English Division 4 | Chester City | 2-2 | Gillingham | 20/08/1960 | 0 | 1 | 0 | 2 | 2 | ||
| 1959/1960 | English Division 4 | Chester City | 4-2 | Gillingham | 06/02/1960 | 0 | 0 | 1 | 2 | 4 | |
| English Division 4 | Gillingham | 3-1 | Chester City | 19/09/1959 | 1 | 0 | 0 | 3 | 1 | ||
| 1958/1959 | English Division 4 | Chester City | 1-2 | Gillingham | 04/04/1959 | 1 | 0 | 0 | 2 | 1 | |
| English Division 4 | Gillingham | 3-3 | Chester City | 17/01/1959 | 0 | 1 | 0 | 3 | 3 | ||