| RETURN TO LEAGUE LISTING | |||||||||||
| Year | Division | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 2005/2006 | Football League 1 | Southend United | Gillingham | ||||||||
| Football League 1 | Gillingham | 1-2 | Southend United | 01/10/2005 | 0 | 0 | 1 | 1 | 2 | ||
| 1997/1998 | English Division 2 | Southend United | 0-0 | Gillingham | 13/04/1998 | 0 | 1 | 0 | 0 | 0 | |
| English Division 2 | Gillingham | 1-2 | Southend United | 13/12/1997 | 0 | 0 | 1 | 1 | 2 | ||
| 1989/1990 | English Division 4 | Southend United | 2-0 | Gillingham | 09/03/1990 | 0 | 0 | 1 | 0 | 2 | |
| English Division 4 | Gillingham | 5-0 | Southend United | 26/09/1989 | 1 | 0 | 0 | 5 | 0 | ||
| 1988/1989 | English Division 3 (old) | Gillingham | 1-1 | Southend United | 25/02/1989 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 (old) | Southend United | 2-1 | Gillingham | 15/10/1988 | 0 | 0 | 1 | 1 | 2 | ||
| 1987/1988 | English Division 3 (old) | Southend United | 1-3 | Gillingham | 01/01/1988 | 1 | 0 | 0 | 3 | 1 | |
| English Division 3 (old) | Gillingham | 8-1 | Southend United | 29/08/1987 | 1 | 0 | 0 | 8 | 1 | ||
| 1983/1984 | English Division 3 (old) | Southend United | 3-1 | Gillingham | 20/04/1984 | 0 | 0 | 1 | 1 | 3 | |
| English Division 3 (old) | Gillingham | 5-1 | Southend United | 26/12/1983 | 1 | 0 | 0 | 5 | 1 | ||
| 1982/1983 | English Division 3 (old) | Southend United | 1-1 | Gillingham | 01/04/1983 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 (old) | Gillingham | 1-0 | Southend United | 27/12/1982 | 1 | 0 | 0 | 1 | 0 | ||
| 1981/1982 | English Division 3 (old) | Gillingham | 2-0 | Southend United | 16/03/1982 | 1 | 0 | 0 | 2 | 0 | |
| English Division 3 (old) | Southend United | 3-0 | Gillingham | 02/11/1981 | 0 | 0 | 1 | 0 | 3 | ||
| 1979/1980 | English Division 3 (old) | Gillingham | 1-0 | Southend United | 13/11/1979 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 (old) | Southend United | 0-3 | Gillingham | 29/10/1979 | 1 | 0 | 0 | 3 | 0 | ||
| 1978/1979 | English Division 3 (old) | Southend United | 0-1 | Gillingham | 14/04/1979 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 (old) | Gillingham | 1-0 | Southend United | 26/12/1978 | 1 | 0 | 0 | 1 | 0 | ||
| 1975/1976 | English Division 3 (old) | Gillingham | 1-2 | Southend United | 13/04/1976 | 0 | 0 | 1 | 1 | 2 | |
| English Division 3 (old) | Southend United | 2-2 | Gillingham | 01/03/1976 | 0 | 1 | 0 | 2 | 2 | ||
| 1974/1975 | English Division 3 (old) | Gillingham | 2-1 | Southend United | 08/02/1975 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 (old) | Southend United | 2-2 | Gillingham | 01/11/1974 | 0 | 1 | 0 | 2 | 2 | ||
| 1971/1972 | English Division 4 | Southend United | 2-2 | Gillingham | 03/05/1972 | 0 | 1 | 0 | 2 | 2 | |
| English Division 4 | Gillingham | 0-0 | Southend United | 29/04/1972 | 0 | 1 | 0 | 0 | 0 | ||
| 1965/1966 | English Division 3 (old) | Gillingham | 1-0 | Southend United | 11/04/1966 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 (old) | Southend United | 5-2 | Gillingham | 08/04/1966 | 0 | 0 | 1 | 2 | 5 | ||
| 1964/1965 | English Division 3 (old) | Southend United | 3-1 | Gillingham | 05/10/1964 | 0 | 0 | 1 | 1 | 3 | |
| English Division 3 (old) | Gillingham | 1-0 | Southend United | 30/09/1964 | 1 | 0 | 0 | 1 | 0 | ||
| 1957/1958 | English Division 3 South | Southend United | 2-0 | Gillingham | 07/04/1958 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 South | Gillingham | 2-0 | Southend United | 04/04/1958 | 1 | 0 | 0 | 2 | 0 | ||
| 1956/1957 | English Division 3 South | Southend United | 5-0 | Gillingham | 22/04/1957 | 0 | 0 | 1 | 0 | 5 | |
| English Division 3 South | Gillingham | 0-2 | Southend United | 19/04/1957 | 0 | 0 | 1 | 0 | 2 | ||
| 1955/1956 | English Division 3 South | Gillingham | 2-3 | Southend United | 27/12/1955 | 0 | 0 | 1 | 2 | 3 | |
| English Division 3 South | Southend United | 2-2 | Gillingham | 26/12/1955 | 0 | 1 | 0 | 2 | 2 | ||
| 1954/1955 | English Division 3 South | Gillingham | 1-1 | Southend United | 23/04/1955 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 South | Southend United | 3-1 | Gillingham | 04/12/1954 | 0 | 0 | 1 | 1 | 3 | ||
| 1953/1954 | English Division 3 South | Gillingham | 3-1 | Southend United | 02/01/1954 | 1 | 0 | 0 | 3 | 1 | |
| English Division 3 South | Southend United | 1-1 | Gillingham | 29/08/1953 | 0 | 1 | 0 | 1 | 1 | ||
| 1952/1953 | English Division 3 South | Southend United | 3-1 | Gillingham | 18/04/1953 | 0 | 0 | 1 | 1 | 3 | |
| English Division 3 South | Gillingham | 1-1 | Southend United | 29/11/1952 | 0 | 1 | 0 | 1 | 1 | ||
| 1951/1952 | English Division 3 South | Southend United | 3-1 | Gillingham | 29/12/1951 | 0 | 0 | 1 | 1 | 3 | |
| English Division 3 South | Gillingham | 2-0 | Southend United | 01/09/1951 | 1 | 0 | 0 | 2 | 0 | ||
| 1950/1951 | English Division 3 South | Southend United | 4-0 | Gillingham | 26/03/1951 | 0 | 0 | 1 | 0 | 4 | |
| English Division 3 South | Gillingham | 0-0 | Southend United | 23/03/1951 | 0 | 1 | 0 | 0 | 0 | ||
| 1937/1938 | English Division 3 South | Gillingham | 2-1 | Southend United | 16/04/1938 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 South | Southend United | 2-0 | Gillingham | 04/12/1937 | 0 | 0 | 1 | 0 | 2 | ||
| 1936/1937 | English Division 3 South | Southend United | 0-2 | Gillingham | 09/01/1937 | 1 | 0 | 0 | 2 | 0 | |
| English Division 3 South | Gillingham | 1-0 | Southend United | 12/09/1936 | 1 | 0 | 0 | 1 | 0 | ||
| 1935/1936 | English Division 3 South | Southend United | 4-2 | Gillingham | 13/04/1936 | 0 | 0 | 1 | 2 | 4 | |
| English Division 3 South | Gillingham | 2-1 | Southend United | 10/04/1936 | 1 | 0 | 0 | 2 | 1 | ||
| 1934/1935 | English Division 3 South | Southend United | 0-0 | Gillingham | 30/03/1935 | 0 | 1 | 0 | 0 | 0 | |
| English Division 3 South | Gillingham | 2-2 | Southend United | 17/11/1934 | 0 | 1 | 0 | 2 | 2 | ||
| 1933/1934 | English Division 3 South | Southend United | 1-2 | Gillingham | 06/09/1933 | 1 | 0 | 0 | 2 | 1 | |
| English Division 3 South | Gillingham | 0-0 | Southend United | 30/08/1933 | 0 | 1 | 0 | 0 | 0 | ||
| 1932/1933 | English Division 3 South | Gillingham | 3-2 | Southend United | 04/02/1933 | 1 | 0 | 0 | 3 | 2 | |
| English Division 3 South | Southend United | 2-2 | Gillingham | 24/09/1932 | 0 | 1 | 0 | 2 | 2 | ||
| 1931/1932 | English Division 3 South | Gillingham | 4-0 | Southend United | 02/01/1932 | 1 | 0 | 0 | 4 | 0 | |
| English Division 3 South | Southend United | 2-0 | Gillingham | 29/08/1931 | 0 | 0 | 1 | 0 | 2 | ||
| 1930/1931 | English Division 3 South | Gillingham | 1-0 | Southend United | 07/02/1931 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 South | Southend United | 3-2 | Gillingham | 04/10/1930 | 0 | 0 | 1 | 2 | 3 | ||
| 1929/1930 | English Division 3 South | Southend United | 0-0 | Gillingham | 21/04/1930 | 0 | 1 | 0 | 0 | 0 | |
| English Division 3 South | Gillingham | 1-0 | Southend United | 18/04/1930 | 1 | 0 | 0 | 1 | 0 | ||
| 1928/1929 | English Division 3 South | Southend United | 2-0 | Gillingham | 01/04/1929 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 South | Gillingham | 0-2 | Southend United | 29/03/1929 | 0 | 0 | 1 | 0 | 2 | ||
| 1927/1928 | English Division 3 South | Gillingham | 1-0 | Southend United | 17/03/1928 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 South | Southend United | 1-2 | Gillingham | 05/11/1927 | 1 | 0 | 0 | 2 | 1 | ||
| 1926/1927 | English Division 3 South | Southend United | 1-0 | Gillingham | 19/03/1927 | 0 | 0 | 1 | 0 | 1 | |
| English Division 3 South | Gillingham | 2-3 | Southend United | 30/10/1926 | 0 | 0 | 1 | 2 | 3 | ||
| 1925/1926 | English Division 3 South | Southend United | 1-1 | Gillingham | 24/04/1926 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 South | Gillingham | 3-1 | Southend United | 20/01/1926 | 1 | 0 | 0 | 3 | 1 | ||
| 1924/1925 | English Division 3 South | Southend United | 4-0 | Gillingham | 26/12/1924 | 0 | 0 | 1 | 0 | 4 | |
| English Division 3 South | Gillingham | 3-1 | Southend United | 25/12/1924 | 1 | 0 | 0 | 3 | 1 | ||
| 1923/1924 | English Division 3 South | Gillingham | 3-2 | Southend United | 05/04/1924 | 1 | 0 | 0 | 3 | 2 | |
| English Division 3 South | Southend United | 3-2 | Gillingham | 29/03/1924 | 0 | 0 | 1 | 2 | 3 | ||
| 1922/1923 | English Division 3 South | Gillingham | 1-0 | Southend United | 07/04/1923 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 South | Southend United | 1-1 | Gillingham | 31/03/1923 | 0 | 1 | 0 | 1 | 1 | ||
| 1921/1922 | English Division 3 South | Southend United | 2-0 | Gillingham | 29/10/1921 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 South | Gillingham | 1-0 | Southend United | 22/10/1921 | 1 | 0 | 0 | 1 | 0 | ||
| 1920/1921 | English Division 3 (old) | Southend United | 1-0 | Gillingham | 28/03/1921 | 0 | 0 | 1 | 0 | 1 | |
| English Division 3 (old) | Gillingham | 1-1 | Southend United | 25/03/1921 | 0 | 1 | 0 | 1 | 1 | ||
| Year | Competition | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 1998/1999 | League Cup 1st Rd 2nd Leg | Gillingham | 0-1 | Southend United | 18/08/1998 | 0 | 0 | 1 | 0 | 1 | |
| League Cup 1st Rd 1st Leg | Southend United | 1-0 | Gillingham | 11/08/1998 | 0 | 0 | 1 | 0 | 1 | ||
| 1989/1990 | AM Cup Southern Section | Southend United | 1-0 | Gillingham | 07/11/1989 | 0 | 0 | 1 | 0 | 1 | |
| 1985/1986 | League Cup 1st Rd 2nd Leg | Gillingham | 2-0 | Southend United | 03/09/1985 | 1 | 0 | 0 | 2 | 0 | |
| League Cup 1st Rd 1st Leg | Southend United | 1-1 | Gillingham | 20/08/1985 | 0 | 1 | 0 | 1 | 1 | ||
| 1969/1970 | FA Cup 1st Rd | Southend United | 0-0 | Gillingham | 15/11/1969 | 0 | 1 | 0 | 0 | 0 | |
| FA Cup 1st Rd Replay | Gillingham | 2-0 | Southend United | 19/11/1969 | 1 | 0 | 0 | 2 | 0 | ||
| 1966/1967 | League Cup 1st Rd Replay | Gillingham | 2-0 | Southend United | 31/08/1966 | aet | 1 | 0 | 0 | 2 | 0 |
| League Cup 1st Rd | Southend United | 0-0 | Gillingham | 24/08/1966 | 0 | 1 | 0 | 0 | 0 | ||
| 1960/1961 | FA Cup 2nd Rd | Gillingham | 3-2 | Southend United | 26/11/1960 | 1 | 0 | 0 | 3 | 2 | |
| 1927/1928 | FA Cup 2nd Rd | Gillingham | 2-0 | Southend United | 10/12/1927 | 1 | 0 | 0 | 2 | 0 | |
| 1925/1926 | FA Cup 2nd Rd | Southend United | 1-0 | Gillingham | 12/12/1925 | 0 | 0 | 1 | 0 | 1 | |
| League | W | D | L | GF | GA | ||||||
| Home | 26 | 8 | 7 | 73 | 34 | ||||||
| Away | 6 | 12 | 22 | 41 | 79 | ||||||