Chesterfield have played Droylsden 2 times in competitive football, winning 0, drawing 1 and losing 1, first meeting on 9 Dec 2008 and most recently on 23 Dec 2008. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 9 Dec 2008 | 2008–09 | FA Cup | H | Droylsden | 2–2 | Jamie Ward 51, Jack Lester 79 | 5,698 |
| 23 Dec 2008 | 2008–09 | FA Cup | A | Droylsden | 1–2 | Jack Lester 35 | 2,824 |
All Chesterfield head-to-head records · Chesterfield season by season