| RETURN TO LEAGUE LISTING | |||||||||||
| Year | Division | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 2005/2006 | Football League 1 | Chesterfield | Gillingham | ||||||||
| Football League 1 | Gillingham | 1-0 | Chesterfield | 27/09/2005 | 1 | 0 | 0 | 1 | 0 | ||
| 1999/2000 | English Division 2 | Gillingham | 1-0 | Chesterfield | 01-04-2000 | 1 | 0 | 0 | 1 | 0 | |
| English Division 2 | Chesterfield | 0-0 | Gillingham | 01-02-2000 | 0 | 1 | 0 | 0 | 0 | ||
| 1998/1999 | English Division 2 | Gillingham | 3-1 | Chesterfield | 06-02-1999 | 1 | 0 | 0 | 3 | 1 | |
| English Division 2 | Chesterfield | 1-0 | Gillingham | 05-09-1998 | 0 | 0 | 1 | 0 | 1 | ||
| 1997/1998 | English Division 2 | Gillingham | 1-0 | Chesterfield | 14-03-1998 | 1 | 0 | 0 | 1 | 0 | |
| English Division 2 | Chesterfield | 1-1 | Gillingham | 04-11-1997 | 0 | 1 | 0 | 1 | 1 | ||
| 1996/1997 | English Division 2 | Chesterfield | 2-2 | Gillingham | 05-04-1997 | 0 | 1 | 0 | 2 | 2 | |
| English Division 2 | Gillingham | 0-1 | Chesterfield | 31-08-1996 | 0 | 0 | 1 | 0 | 1 | ||
| 1994/1995 | English Division 3 | Chesterfield | 2-0 | Gillingham | 11-02-1995 | 0 | 0 | 1 | 0 | 2 | |
| English Division 3 | Gillingham | 1-1 | Chesterfield | 19-11-1994 | 0 | 1 | 0 | 1 | 1 | ||
| 1993/1994 | English Division 3 | Chesterfield | 3-2 | Gillingham | 18-12-1993 | 0 | 0 | 1 | 2 | 3 | |
| English Division 3 | Gillingham | 0-2 | Chesterfield | 14-08-1993 | 0 | 0 | 1 | 0 | 2 | ||
| 1992/1993 | English Division 3 | Chesterfield | 1-1 | Gillingham | 16-02-1993 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 | Gillingham | 0-0 | Chesterfield | 12-09-1992 | 0 | 1 | 0 | 0 | 0 | ||
| 1991/1992 | English Division 4 | Chesterfield | 3-3 | Gillingham | 25-04-1992 | 0 | 1 | 0 | 3 | 3 | |
| English Division 4 | Gillingham | 0-1 | Chesterfield | 05-10-1991 | 0 | 0 | 1 | 0 | 1 | ||
| 1990/1991 | English Division 4 | Gillingham | 0-1 | Chesterfield | 02-03-1991 | 0 | 0 | 1 | 0 | 1 | |
| English Division 4 | Chesterfield | 1-1 | Gillingham | 01-12-1990 | 0 | 1 | 0 | 1 | 1 | ||
| 1989/1990 | English Division 4 | Chesterfield | 2-0 | Gillingham | 31-03-1990 | 0 | 0 | 1 | 0 | 2 | |
| English Division 4 | Gillingham | 3-0 | Chesterfield | 21-10-1989 | 1 | 0 | 0 | 3 | 0 | ||
| 1988/1989 | English Division 3 (old) | Chesterfield | 3-1 | Gillingham | 18-02-1989 | 0 | 0 | 1 | 1 | 3 | |
| English Division 3 (old) | Gillingham | 0-1 | Chesterfield | 08-10-1988 | 0 | 0 | 1 | 0 | 1 | ||
| 1987/1988 | English Division 3 (old) | Chesterfield | 1-4 | Gillingham | 06-02-1988 | 1 | 0 | 0 | 4 | 1 | |
| English Division 3 (old) | Gillingham | 10-0 | Chesterfield | 05-09-1987 | 1 | 0 | 0 | 10 | 0 | ||
| 1986/1987 | English Division 3 (old) | Chesterfield | 1-0 | Gillingham | 03-03-1987 | 0 | 0 | 1 | 0 | 1 | |
| English Division 3 (old) | Gillingham | 3-0 | Chesterfield | 01-11-1986 | 1 | 0 | 0 | 3 | 0 | ||
| 1985/1986 | English Division 3 (old) | Chesterfield | 1-1 | Gillingham | 25-01-1986 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 (old) | Gillingham | 1-1 | Chesterfield | 14-09-1985 | 0 | 1 | 0 | 1 | 1 | ||
| 1982/1983 | English Division 3 (old) | Gillingham | 3-1 | Chesterfield | 15-02-1983 | 1 | 0 | 0 | 3 | 1 | |
| English Division 3 (old) | Chesterfield | 1-2 | Gillingham | 02-11-1982 | 1 | 0 | 0 | 2 | 1 | ||
| 1981/1982 | English Division 3 (old) | Chesterfield | 1-3 | Gillingham | 15-05-1982 | 1 | 0 | 0 | 3 | 1 | |
| English Division 3 (old) | Gillingham | 3-2 | Chesterfield | 06-04-1982 | 1 | 0 | 0 | 3 | 2 | ||
| 1980/1981 | English Division 3 (old) | Gillingham | 1-0 | Chesterfield | 24-01-1981 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 (old) | Chesterfield | 2-0 | Gillingham | 30-08-1980 | 0 | 0 | 1 | 0 | 2 | ||
| 1979/1980 | English Division 3 (old) | Chesterfield | 0-0 | Gillingham | 01-04-1980 | 0 | 1 | 0 | 0 | 0 | |
| English Division 3 (old) | Gillingham | 0-1 | Chesterfield | 26-02-1980 | 0 | 0 | 1 | 0 | 1 | ||
| 1978/1979 | English Division 3 (old) | Chesterfield | 0-2 | Gillingham | 19-05-1979 | 1 | 0 | 0 | 2 | 0 | |
| English Division 3 (old) | Gillingham | 2-1 | Chesterfield | 30-09-1978 | 1 | 0 | 0 | 2 | 1 | ||
| 1977/1978 | English Division 3 (old) | Chesterfield | 5-2 | Gillingham | 26-04-1978 | 0 | 0 | 1 | 2 | 5 | |
| English Division 3 (old) | Gillingham | 3-0 | Chesterfield | 27-09-1977 | 1 | 0 | 0 | 3 | 0 | ||
| 1976/1977 | English Division 3 (old) | Chesterfield | 1-0 | Gillingham | 12-03-1977 | 0 | 0 | 1 | 0 | 1 | |
| English Division 3 (old) | Gillingham | 2-1 | Chesterfield | 02-10-1976 | 1 | 0 | 0 | 2 | 1 | ||
| 1975/1976 | English Division 3 (old) | Chesterfield | 0-1 | Gillingham | 31-01-1976 | 1 | 0 | 0 | 1 | 0 | |
| English Division 3 (old) | Gillingham | 2-2 | Chesterfield | 21/10/1975 | 0 | 1 | 0 | 2 | 2 | ||
| 1974/1975 | English Division 3 (old) | Chesterfield | 2-1 | Gillingham | 29/03/1975 | 0 | 0 | 1 | 1 | 2 | |
| English Division 3 (old) | Gillingham | 4-0 | Chesterfield | 21/12/1974 | 1 | 0 | 0 | 4 | 0 | ||
| 1970/1971 | English Division 3 (old) | Gillingham | 1-1 | Chesterfield | 28/04/1971 | 0 | 1 | 0 | 1 | 1 | |
| English Division 3 (old) | Chesterfield | 2-0 | Gillingham | 02/09/1970 | 0 | 0 | 1 | 0 | 2 | ||
| 1963/1964 | English Division 4 | Gillingham | 1-0 | Chesterfield | 28/12/1963 | 1 | 0 | 0 | 1 | 0 | |
| English Division 4 | Chesterfield | 0-3 | Gillingham | 26/12/1963 | 1 | 0 | 0 | 3 | 0 | ||
| 1962/1963 | English Division 4 | Chesterfield | 0-2 | Gillingham | 29/04/1963 | 1 | 0 | 0 | 2 | 0 | |
| English Division 4 | Gillingham | 2-1 | Chesterfield | 26/12/1962 | 1 | 0 | 0 | 2 | 1 | ||
| 1961/1962 | English Division 4 | Gillingham | 5-1 | Chesterfield | 20/01/1962 | 1 | 0 | 0 | 5 | 1 | |
| English Division 4 | Chesterfield | 3-2 | Gillingham | 09/09/1961 | 0 | 0 | 1 | 2 | 3 | ||
| League | W | D | L | GF | GA | ||||||
| Home | 17 | 5 | 6 | 53 | 20 | ||||||
| Away | 7 | 8 | 12 | 34 | 39 | ||||||