| RETURN TO LEAGUE LISTING | |||||||||||
| Year | Division | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| Never Played in Football League | |||||||||||
| Year | Competition | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 2002/2003 | League Cup 3rd Rd | Chelsea | 2-1 | Gillingham | 06/11/2002 | 0 | 0 | 1 | 1 | 2 | |
| 2000/2001 | FA Cup 4th Rd | Gillingham | 2-4 | Chelsea | 28/01/2001 | Live TV | 0 | 0 | 1 | 2 | 4 |
| 1999/2000 | FA Cup 6th Rd | Chelsea | 5-0 | Gillingham | 20/02/2000 | 0 | 0 | 1 | 0 | 5 | |
| 1983/1984 | League Cup 1st Rd 2nd Leg | Chelsea | 4-0 | Gillingham | 13/09/1983 | 0 | 0 | 1 | 0 | 4 | |
| League Cup 1st Rd 1st Leg | Gillingham | 1-2 | Chelsea | 30/08/1983 | 0 | 0 | 1 | 1 | 2 | ||