Chelsea have played Gillingham 5 times in competitive football, winning 5, drawing 0 and losing 0, first meeting on 30 Aug 1983 and most recently on 6 Nov 2002. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 30 Aug 1983 | 1983–84 | League Cup | A | Gillingham | 2–1 | Clive Walker 38, Kerry Dixon 57 | 8,633 |
| 13 Sep 1983 | 1983–84 | League Cup | H | Gillingham | 4–0 | Kerry Dixon 40, Kerry Dixon 44, Kerry Dixon 54, Kerry Dixon 84 | 9,704 |
| 20 Feb 2000 | 1999–00 | FA Cup | H | Gillingham | 5–0 | Tore André Flo, John Terry, George Weah, Gianfranco Zola, Jody Morris | 34,205 |
| 28 Jan 2001 | 2000–01 | FA Cup | A | Gillingham | 4–2 | Eiður Guðjohnsen 3, Jesper Gronkjaer 13, Jesper Gronkjaer 24, Eiður Guðjohnsen 90 | 10,419 |
| 6 Nov 2002 | 2002–03 | League Cup | H | Gillingham | 2–1 | Carlton Cole 20, Carlton Cole 52 | 28,033 |
See also: the Gillingham archive and Gillingham v Chelsea.