Chelsea have played Chesterfield 8 times in competitive football, winning 5, drawing 2 and losing 1, first meeting on 21 Oct 1905 and most recently on 8 Jan 2022. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 21 Oct 1905 | 1905–06 | Second Division | H | Chesterfield | 0–1 | 10,000 | |
| 24 Feb 1906 | 1905–06 | Second Division | A | Chesterfield | 2–0 | FH Pearson, JH Kirwan | |
| 1 Dec 1906 | 1906–07 | Second Division | A | Chesterfield | 0–0 | ||
| 6 Apr 1907 | 1906–07 | Second Division | H | Chesterfield | 7–1 | ||
| 4 Feb 1911 | 1910–11 | FA Cup | H | Chesterfield | 4–1 | ||
| 11 Feb 1950 | 1949–50 | FA Cup | A | Chesterfield | 1–1 | JD Bowie 35 | |
| 15 Feb 1950 | 1949–50 | FA Cup | H | Chesterfield | 3–0 | TFR Bentley 74, TFR Bentley 79, HJR Billington 89 | |
| 8 Jan 2022 | 2021–22 | FA Cup | H | Chesterfield | 5–1 | Timo Werner 6, Callum Hudson-Odoi 18, Romelu Lukaku 20, Andreas Christensen 39, Hakim Ziyech 55 | 39,795 |
See also: the Chesterfield archive and Chesterfield v Chelsea.