| RETURN TO LEAGUE LISTING | |||||||||||
| Year | Division | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 1995/1996 | English Division 3 | Gillingham | 1-1 | Leyton Orient | 23/03/1996 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 | Leyton Orient | 0-1 | Gillingham | 01/01/1996 | 1 | 0 | 0 | 1 | 0 | ||
| 1984/1985 | English Division 3 (old) | Gillingham | 2-0 | Leyton Orient | 12/01/1985 | 1 | 0 | 0 | 2 | 0 | |
| English Division 3 (old) | Leyton Orient | 2-4 | Gillingham | 01/09/1984 | 1 | 0 | 0 | 4 | 2 | ||
| 1983/1984 | English Division 3 (old) | Gillingham | 3-1 | Leyton Orient | 31/03/1984 | 1 | 0 | 0 | 3 | 1 | |
| English Division 3 (old) | Leyton Orient | 1-1 | Gillingham | 24/10/1983 | 0 | 1 | 0 | 1 | 1 | ||
| 1982/1983 | English Division 3 (old) | Leyton Orient | 2-0 | Gillingham | 01/03/1983 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 (old) | Gillingham | 4-0 | Leyton Orient | 19/10/1982 | 1 | 0 | 0 | 4 | 0 | ||
| 1969/1970 | English Division 3 (old) | Leyton Orient | 1-2 | Gillingham | 27/04/1970 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 (old) | Gillingham | 0-1 | Leyton Orient | 25/10/1969 | 0 | 0 | 1 | 0 | 1 | ||
| 1968/1969 | English Division 3 (old) | Leyton Orient | 1-1 | Gillingham | 08/03/1969 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 (old) | Gillingham | 2-2 | Leyton Orient | 17/08/1968 | 0 | 1 | 0 | 2 | 2 | ||
| 1967/1968 | English Division 3 (old) | Leyton Orient | 0-4 | Gillingham | 07/05/1968 | 1 | 0 | 0 | 4 | 0 | |
| English Division 3 (old) | Gillingham | 2-3 | Leyton Orient | 09/03/1968 | 0 | 0 | 1 | 2 | 3 | ||
| 1966/1967 | English Division 3 (old) | Gillingham | 0-0 | Leyton Orient | 14/01/1967 | 0 | 1 | 0 | 0 | 0 | |
| English Division 3 (old) | Leyton Orient | 0-1 | Gillingham | 09/09/1966 | 1 | 0 | 0 | 1 | 0 | ||
| 1955/1956 | English Division 3 South | Leyton Orient | 2-0 | Gillingham | 01/09/1955 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 South | Gillingham | 0-1 | Leyton Orient | 24/08/1955 | 0 | 0 | 1 | 0 | 1 | ||
| 1954/1955 | English Division 3 South | Leyton Orient | 2-2 | Gillingham | 12/02/1955 | 0 | 1 | 0 | 2 | 2 | |
| English Division 3 South | Gillingham | 0-0 | Leyton Orient | 25/09/1954 | 0 | 1 | 0 | 0 | 0 | ||
| 1953/1954 | English Division 3 South | Gillingham | 1-2 | Leyton Orient | 30/09/1953 | 0 | 0 | 1 | 1 | 2 | |
| English Division 3 South | Leyton Orient | 3-1 | Gillingham | 24/09/1953 | 0 | 0 | 1 | 1 | 3 | ||
| 1952/1953 | English Division 3 South | Leyton Orient | 1-1 | Gillingham | 21/03/1953 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 South | Gillingham | 3-2 | Leyton Orient | 01/11/1952 | 1 | 0 | 0 | 3 | 2 | ||
| 1951/1952 | English Division 3 South | Gillingham | 1-1 | Leyton Orient | 08/03/1952 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 South | Leyton Orient | 1-0 | Gillingham | 20/10/1951 | 0 | 0 | 1 | 0 | 1 | ||
| 1950/1951 | English Division 3 South | Gillingham | 1-0 | Leyton Orient | 03/02/1951 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 South | Leyton Orient | 4-0 | Gillingham | 23/09/1950 | 0 | 0 | 1 | 0 | 4 | ||
| 1937/1938 | English Division 3 South | Leyton Orient | 3-0 | Gillingham | 23/04/1938 | 0 | 0 | 1 | 0 | 3 | |
| English Division 3 South | Gillingham | 1-2 | Leyton Orient | 23/02/1938 | 0 | 0 | 1 | 1 | 2 | ||
| 1936/1937 | English Division 3 South | Gillingham | 0-2 | Leyton Orient | 03/04/1937 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 South | Leyton Orient | 2-0 | Gillingham | 16/01/1937 | 0 | 0 | 1 | 0 | 2 | ||
| 1935/1936 | English Division 3 South | Gillingham | 3-0 | Leyton Orient | 26/12/1935 | 1 | 0 | 0 | 3 | 0 | |
| English Division 3 South | Leyton Orient | 3-1 | Gillingham | 25/12/1935 | 0 | 0 | 1 | 1 | 3 | ||
| 1934/1935 | English Division 3 South | Gillingham | 1-0 | Leyton Orient | 22/04/1935 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 South | Leyton Orient | 2-2 | Gillingham | 19/04/1935 | 0 | 1 | 0 | 2 | 2 | ||
| 1933/1934 | English Division 3 South | Gillingham | 1-1 | Leyton Orient | 17/03/1934 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 South | Leyton Orient | 2-1 | Gillingham | 04/11/1933 | 0 | 0 | 1 | 1 | 2 | ||
| 1932/1933 | English Division 3 South | Leyton Orient | 1-2 | Gillingham | 15/04/1933 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 South | Gillingham | 3-1 | Leyton Orient | 03/12/1932 | 1 | 0 | 0 | 3 | 1 | ||
| 1931/1932 | English Division 3 South | Gillingham | 0-2 | Leyton Orient | 02/04/1932 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 South | Leyton Orient | 3-1 | Gillingham | 21/11/1931 | 0 | 0 | 1 | 1 | 3 | ||
| 1930/1931 | English Division 3 South | Leyton Orient | 0-2 | Gillingham | 21/02/1931 | 1 | 0 | 0 | 2 | 0 | |
| English Division 3 South | Gillingham | 0-0 | Leyton Orient | 18/10/1930 | 0 | 1 | 0 | 0 | 0 | ||
| 1929/1930 | English Division 3 South | Leyton Orient | 2-0 | Gillingham | 22/03/1930 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 South | Gillingham | 2-0 | Leyton Orient | 16/11/1929 | 1 | 0 | 0 | 2 | 0 | ||
| Year | Competition | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 1992/1993 | AM Cup Southern Section | Leyton Orient | 4-1 | Gillingham | 01/12/1992 | 0 | 0 | 1 | 1 | 4 | |
| 1989/1990 | League Cup 1st Rd 2nd Leg | Leyton Orient | 3-0 | Gillingham | 29/08/1989 | 0 | 0 | 1 | 0 | 3 | |
| League Cup 1st Rd 1st Leg | Gillingham | 1-4 | Leyton Orient | 22/08/1989 | 0 | 0 | 1 | 1 | 4 | ||
| 1987/1988 | AM Cup Southern Section | Gillingham | 2-2 | Leyton Orient | 27/10/1987 | 0 | 1 | 0 | 2 | 2 | |
| 1982/1983 | League Cup 1st Rd 2nd Leg | Leyton Orient | 2-0 | Gillingham | 15/09/1982 | 0 | 0 | 1 | 0 | 2 | |
| League Cup 1st Rd 1st Leg | Gillingham | 3-0 | Leyton Orient | 31/08/1982 | 1 | 0 | 0 | 3 | 0 | ||
| 1968/1969 | League Cup 1st Rd | Gillingham | 2-2 | Leyton Orient | 14/08/1968 | 0 | 1 | 0 | 2 | 2 | |
| League Cup 1st Rd Replay | Leyton Orient | 3-0 | Gillingham | 20/08/1968 | 0 | 0 | 1 | 0 | 3 | ||
| 1968/1969 | FA Cup 1st Rd | Leyton Orient | 1-1 | Gillingham | 16/11/1968 | 0 | 1 | 0 | 1 | 1 | |
| FA Cup 1st Rd Replay | Gillingham | 2-1 | Leyton Orient | 20/11/1968 | 1 | 0 | 0 | 2 | 1 | ||
| 1967/1968 | League Cup 1st Rd | Leyton Orient | 1-3 | Gillingham | 22/08/1967 | 1 | 0 | 0 | 3 | 1 | |
| 1960/1961 | FA Cup 3rd Rd | Gillingham | 2-6 | Leyton Orient | 07/01/1961 | 0 | 0 | 1 | 2 | 6 | |
| 1947/1948 | FA Cup 1st Rd | Gillingham | 1-0 | Leyton Orient | 29/11/1947 | 1 | 0 | 0 | 1 | 0 | |