Chesterfield have played Maidstone United 6 times in competitive football, winning 4, drawing 0 and losing 2, first meeting on 23 Sep 1989 and most recently on 26 Dec 1991. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 23 Sep 1989 | 1989–90 | Fourth Division | A | Maidstone United | 1–0 | ||
| 3 Feb 1990 | 1989–90 | Fourth Division | H | Maidstone United | 3–1 | Gunn 6, Brien 21, Brien 60 | |
| 1 Jan 1991 | 1990–91 | Fourth Division | A | Maidstone United | 0–1 | ||
| 13 Apr 1991 | 1990–91 | Fourth Division | H | Maidstone United | 1–2 | Lancaster 53 | |
| 17 Aug 1991 | 1991–92 | Fourth Division | H | Maidstone United | 3–0 | Williams 39, Jamie Hewitt 63, Jamie Hewitt 80 | |
| 26 Dec 1991 | 1991–92 | Fourth Division | A | Maidstone United | 1–0 | Cooke 10 |
All Chesterfield head-to-head records · Chesterfield season by season