| 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 | ||
| 2001/02 | FA Cup 5th Rd | Arsenal | 5-2 | Gillingham | 17/02/2002 | 0 | 0 | 1 | 2 | 5 | |
| 1966/67 | League Cup 2nd Rd 2nd Replay | Arsenal | 5-0 | Gillingham | 28/09/1966 | 0 | 0 | 1 | 0 | 5 | |
| League Cup 2nd Rd Replay | Gillingham | 1-1 | Arsenal | 21/09/1966 | aet | 0 | 1 | 0 | 1 | 1 | |
| League Cup 2nd Round | Arsenal | 1-1 | Gillingham | 13/09/1966 | 0 | 1 | 0 | 1 | 1 | ||
| 1899/00 | FA Cup 3rd Qualifying Rd 4th Replay | Woolwich Arsenal | 0-1 | Gillingham | 14/11/1899 | at Gravesend | 1 | 0 | 0 | 1 | 0 |
| FA Cup 3rd Qualifying Rd 3rd Replay | Gillingham | 1-1 | Woolwich Arsenal | 08/11/1899 | at Tottenham | 0 | 1 | 0 | 1 | 1 | |
| FA Cup 3rd Qualifying Rd 2nd Replay | Woolwich Arsenal | 2-2 | Gillingham | 06/11/1899 | at Millwall | 0 | 1 | 0 | 2 | 2 | |
| FA Cup 3rd Qualifying Rd 1st Replay | Woolwich Arsenal | 0-0 | Gillingham | 01/11/1899 | 0 | 1 | 0 | 0 | 0 | ||
| FA Cup 3rd Qualifying Rd | Gillingham | 1-1 | Woolwich Arsenal | 28/10/1899 | 0 | 1 | 0 | 1 | 1 | ||
| 1897/98 | FA Cup 5th Qualifying Rd | Woolwich Arsenal | 4-2 | Gillingham | 11/12/1897 | 0 | 0 | 1 | 2 | 4 | |