Arsenal have played Chesterfield 11 times in competitive football, winning 8, drawing 1 and losing 2, first meeting on 7 Oct 1899 and most recently on 16 Jan 1937. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 7 Oct 1899 | 1899–00 | Second Division | A | Chesterfield | 1–3 | Jack Aston | |
| 10 Feb 1900 | 1899–00 | Second Division | H | Chesterfield | 2–0 | John Dick, Andrew McCowie | |
| 29 Sep 1900 | 1900–01 | Second Division | H | Chesterfield | 1–0 | Sandy Main | |
| 19 Feb 1901 | 1900–01 | Second Division | A | Chesterfield | 1–0 | Ralph Gaudie | |
| 5 Oct 1901 | 1901–02 | Second Division | H | Chesterfield | 3–2 | Jimmy Laidlaw, Logan | |
| 1 Feb 1902 | 1901–02 | Second Division | A | Chesterfield | 3–1 | John Dick, Sandy Main, Walter Anderson | |
| 14 Mar 1903 | 1902–03 | Second Division | A | Chesterfield | 2–2 | Tim Coleman, Tim Coleman | |
| 10 Apr 1903 | 1902–03 | Second Division | H | Chesterfield | 3–0 | Tommy Briercliffe, Bill Gooing | |
| 21 Nov 1903 | 1903–04 | Second Division | H | Chesterfield | 6–0 | Tommy Briercliffe, Tim Coleman, Bill Gooing, Billy Linward | |
| 19 Mar 1904 | 1903–04 | Second Division | A | Chesterfield | 0–1 | ||
| 16 Jan 1937 | 1936–37 | FA Cup | A | Chesterfield | 5–1 | Alf Kirchen, Alf Kirchen, Ted Drake, Ted Drake, Bobby Davidson | 21,786 |
See also: the Chesterfield archive and Chesterfield v Arsenal.