| RETURN TO LEAGUE LISTING | |||||||||||
| Year | Division | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 2005/2006 | Football League 1 | Colchester United | 5-0 | Gillingham | 26/11/2005 | 0 | 0 | 1 | 0 | 5 | |
| Football League 1 | Gillingham | 2-1 | Colchester United | 06/08/2005 | 1 | 0 | 0 | 2 | 1 | ||
| 1999/2000 | English Division 2 | Colchester United | 2-1 | Gillingham | 25-03-2000 | 0 | 0 | 1 | 1 | 2 | |
| English Division 2 | Gillingham | 2-1 | Colchester United | 26-12-1999 | 1 | 0 | 0 | 2 | 1 | ||
| 1998/1999 | English Division 2 | Gillingham | 1-1 | Colchester United | 20-02-1999 | 0 | 1 | 0 | 1 | 1 | |
| English Division 2 | Colchester United | 1-1 | Gillingham | 12-09-1998 | 0 | 1 | 0 | 1 | 1 | ||
| 1995/1996 | English Division 3 | Colchester United | 1-1 | Gillingham | 16-04-1996 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 | Gillingham | 0-1 | Colchester United | 02-09-1995 | 0 | 0 | 1 | 0 | 1 | ||
| 1994/1995 | English Division 3 | Gillingham | 1-3 | Colchester United | 11-04-1995 | 0 | 0 | 1 | 1 | 3 | |
| English Division 3 | Colchester United | 2-2 | Gillingham | 05-11-1994 | 0 | 1 | 0 | 2 | 2 | ||
| 1993/1994 | English Division 3 | Colchester United | 1-2 | Gillingham | 29-01-1994 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 | Gillingham | 3-0 | Colchester United | 30-10-1993 | 1 | 0 | 0 | 3 | 0 | ||
| 1992/1993 | English Division 3 | Colchester United | 3-0 | Gillingham | 16-04-1993 | 0 | 0 | 1 | 0 | 3 | |
| English Division 3 | Gillingham | 0-1 | Colchester United | 18-12-1992 | 0 | 0 | 1 | 0 | 1 | ||
| 1989/1990 | English Division 4 | Colchester United | 2-0 | Gillingham | 23-02-1990 | 0 | 0 | 1 | 0 | 2 | |
| English Division 4 | Gillingham | 3-3 | Colchester United | 24-11-1989 | 0 | 1 | 0 | 3 | 3 | ||
| 1980/1981 | English Division 3 (old) | Gillingham | 0-0 | Colchester United | 18-04-1981 | 0 | 1 | 0 | 0 | 0 | |
| English Division 3 (old) | Colchester United | 2-1 | Gillingham | 27-12-1980 | 0 | 0 | 1 | 1 | 2 | ||
| 1979/1980 | English Division 3 (old) | Gillingham | 2-2 | Colchester United | 05-04-1980 | 0 | 1 | 0 | 2 | 2 | |
| English Division 3 (old) | Colchester United | 2-2 | Gillingham | 26-12-1979 | 0 | 1 | 0 | 2 | 2 | ||
| 1978/1979 | English Division 3 (old) | Colchester United | 2-2 | Gillingham | 07-05-1979 | 0 | 1 | 0 | 2 | 2 | |
| English Division 3 (old) | Gillingham | 3-0 | Colchester United | 16-04-1979 | 1 | 0 | 0 | 3 | 0 | ||
| 1977/1978 | English Division 3 (old) | Colchester United | 1-1 | Gillingham | 13-01-1978 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 (old) | Gillingham | 1-3 | Colchester United | 20-08-1977 | 0 | 0 | 1 | 1 | 3 | ||
| 1975/1976 | English Division 3 (old) | Colchester United | 2-2 | Gillingham | 20-03-1976 | 0 | 1 | 0 | 2 | 2 | |
| English Division 3 (old) | Gillingham | 0-1 | Colchester United | 29-11-1975 | 0 | 0 | 1 | 0 | 1 | ||
| 1974/1975 | English Division 3 (old) | Gillingham | 2-1 | Colchester United | 12-04-1975 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 (old) | Colchester United | 4-2 | Gillingham | 05-10-1974 | 0 | 0 | 1 | 2 | 4 | ||
| 1973/1974 | English Division 4 | Colchester United | 0-2 | Gillingham | 20-04-1974 | 1 | 0 | 0 | 2 | 0 | |
| English Division 4 | Gillingham | 4-1 | Colchester United | 08-12-1973 | 1 | 0 | 0 | 4 | 1 | ||
| 1972/1973 | English Division 4 | Colchester United | 4-0 | Gillingham | 30-04-1973 | 0 | 0 | 1 | 0 | 4 | |
| English Division 4 | Gillingham | 2-1 | Colchester United | 06-04-1973 | 1 | 0 | 0 | 2 | 1 | ||
| 1971/1972 | English Division 4 | Gillingham | 0-2 | Colchester United | 19-02-1972 | 0 | 0 | 1 | 0 | 2 | |
| English Division 4 | Colchester United | 2-2 | Gillingham | 29-10-1971 | 0 | 1 | 0 | 2 | 2 | ||
| 1967/1968 | English Division 3 (old) | Gillingham | 1-0 | Colchester United | 13-04-1968 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 (old) | Colchester United | 2-2 | Gillingham | 18/11/1967 | 0 | 1 | 0 | 2 | 2 | ||
| 1966/1967 | English Division 3 (old) | Colchester United | 0-0 | Gillingham | 11-03-1967 | 0 | 1 | 0 | 0 | 0 | |
| English Division 3 (old) | Gillingham | 2-1 | Colchester United | 18-02-1967 | 1 | 0 | 0 | 2 | 1 | ||
| 1964/1965 | English Division 3 (old) | Colchester United | 2-1 | Gillingham | 28-12-1964 | 0 | 0 | 1 | 1 | 2 | |
| English Division 3 (old) | Gillingham | 2-1 | Colchester United | 26-12-1964 | 1 | 0 | 0 | 2 | 1 | ||
| 1961/1962 | English Division 4 | Colchester United | 6-0 | Gillingham | 10-03-1962 | 0 | 0 | 1 | 0 | 6 | |
| English Division 4 | Gillingham | 2-1 | Colchester United | 21-10-1961 | 1 | 0 | 0 | 2 | 1 | ||
| 1957/1958 | English Division 3 South | Colchester United | 3-2 | Gillingham | 01-03-1958 | 0 | 0 | 1 | 2 | 3 | |
| English Division 3 South | Gillingham | 2-3 | Colchester United | 19-10-1957 | 0 | 0 | 1 | 2 | 3 | ||
| 1956/1957 | English Division 3 South | Gillingham | 1-2 | Colchester United | 23-03-1957 | 0 | 0 | 1 | 1 | 2 | |
| English Division 3 South | Colchester United | 0-0 | Gillingham | 10-11-1956 | 0 | 1 | 0 | 0 | 0 | ||
| 1955/1956 | English Division 3 South | Gillingham | 2-1 | Colchester United | 25-04-1956 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 South | Colchester United | 1-1 | Gillingham | 29-09-1955 | 0 | 1 | 0 | 1 | 1 | ||
| 1954/1955 | English Division 3 South | Colchester United | 2-2 | Gillingham | 28-04-1955 | 0 | 1 | 0 | 2 | 2 | |
| English Division 3 South | Gillingham | 2-1 | Colchester United | 09-04-1955 | 1 | 0 | 0 | 2 | 1 | ||
| 1953/1954 | English Division 3 South | Colchester United | 0-1 | Gillingham | 06-03-1954 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 South | Gillingham | 2-0 | Colchester United | 17-10-1953 | 1 | 0 | 0 | 2 | 0 | ||
| 1952/1953 | English Division 3 South | Gillingham | 1-1 | Colchester United | 21-02-1953 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 South | Colchester United | 1-1 | Gillingham | 04-10-1952 | 0 | 1 | 0 | 1 | 1 | ||
| 1951/1952 | English Division 3 South | Colchester United | 1-0 | Gillingham | 26-12-1951 | 0 | 0 | 1 | 0 | 1 | |
| English Division 3 South | Gillingham | 1-2 | Colchester United | 25-12-1951 | 0 | 0 | 1 | 1 | 2 | ||
| 1950/1951 | English Division 3 South | Colchester United | 4-2 | Gillingham | 16-12-1950 | 0 | 0 | 1 | 2 | 4 | |
| English Division 3 South | Gillingham | 0-0 | Colchester United | 19-08-1950 | 0 | 1 | 0 | 0 | 0 | ||
| Year | Competition | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 1998/1999 | AM Cup 2nd Rd South | Colchester United | 1-5 | Gillingham | 05-12-1998 | 1 | 0 | 0 | 5 | 1 | |
| 1993/1994 | AM Cup Southern Section | Gillingham | 0-0 | Colchester United | 28/09/1993 | 0 | 1 | 0 | 0 | 0 | |
| 1992/1993 | FA Cup 2nd Rd Replay | Colchester United | 2-3 | Gillingham | 16-12-1992 | 1 | 0 | 0 | 3 | 2 | |
| FA Cup 2nd Rd | Gillingham | 1-1 | Colchester United | 05-12-1992 | 0 | 1 | 0 | 1 | 1 | ||
| 1986/1987 | AM Cup 1st Rd South | Gillingham | 2-0 | Colchester United | 26/01/1987 | 1 | 0 | 0 | 2 | 0 | |
| 1984/1985 | FA Cup 2nd Rd | Colchester United | 0-5 | Gillingham | 08-12-1984 | 1 | 0 | 0 | 5 | 0 | |
| League Cup 1st Rd 2nd Leg | Colchester United | 0-2 | Gillingham | 04-09-1984 | 1 | 0 | 0 | 2 | 0 | ||
| League Cup 1st Rd 1st Leg | Gillingham | 3-2 | Colchester United | 28-08-1984 | 1 | 0 | 0 | 3 | 2 | ||
| AM Cup 1st Rd 2nd Leg South | Colchester United | 2-0 | Gillingham | 05/02/1985 | 0 | 0 | 1 | 0 | 2 | ||
| AM Cup 1st Rd 1st Leg South | Gillingham | 2-2 | Colchester United | 23/01/1985 | 0 | 1 | 0 | 2 | 2 | ||
| 1981/1982 | League Cup 1st Rd 2nd Leg | Colchester United | 2-0 | Gillingham | 01/09/1981 | 0 | 0 | 1 | 0 | 2 | |
| League Cup 1st Rd 1st Leg | Gillingham | 1-1 | Colchester United | 15/09/1981 | 0 | 1 | 0 | 1 | 1 | ||
| 1980/1981 | League Cup 1st Rd 2nd Leg | Gillingham | 2-1 | Colchester United | 12/08/1980 | ||||||