Cheltenham Town have played Chesterfield 20 times in competitive football, winning 3, drawing 5 and losing 12, first meeting on 9 Sep 2000 and most recently on 3 Apr 2026. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 9 Sep 2000 | 2000–01 | Third Division | H | Chesterfield | 0–1 | ||
| 9 Feb 2001 | 2000–01 | Third Division | A | Chesterfield | 0–2 | ||
| 28 Dec 2002 | 2002–03 | Second Division | A | Chesterfield | 2–2 | Spencer 55, Spencer 70 | |
| 25 Jan 2003 | 2002–03 | Second Division | H | Chesterfield | 0–0 | ||
| 18 Nov 2006 | 2006–07 | League One | A | Chesterfield | 0–1 | ||
| 9 Apr 2007 | 2006–07 | League One | H | Chesterfield | 0–0 | ||
| 12 Dec 2009 | 2009–10 | League Two | A | Chesterfield | 0–1 | 3,145 | |
| 6 Mar 2010 | 2009–10 | League Two | H | Chesterfield | 0–1 | 3,006 | |
| 18 Sep 2010 | 2010–11 | League Two | A | Chesterfield | 0–3 | 5,503 | |
| 5 Mar 2011 | 2010–11 | League Two | H | Chesterfield | 0–3 | 2,870 | |
| 20 Nov 2012 | 2012–13 | League Two | A | Chesterfield | 1–4 | Mohamed 57 | 4,333 |
| 5 Mar 2013 | 2012–13 | League Two | H | Chesterfield | 1–0 | Benson 90+2 | 2,195 |
| 10 Aug 2013 | 2013–14 | League Two | A | Chesterfield | 0–2 | 5,367 | |
| 25 Feb 2014 | 2013–14 | League Two | H | Chesterfield | 1–4 | Byron Harrison 57 | 2,317 |
| 30 Sep 2017 | 2017–18 | League Two | A | Chesterfield | 2–0 | ||
| 17 Mar 2018 | 2017–18 | League Two | H | Chesterfield | 1–1 | ||
| 21 Sep 2024 | 2024–25 | League Two | A | Chesterfield | 1–1 | Arkell Jude-Boyd 53 | 7,652 |
| 1 Feb 2025 | 2024–25 | League Two | H | Chesterfield | 1–0 | Arkell Jude-Boyd 90+2 | 3,869 |
| 9 Aug 2025 | 2025–26 | League Two | H | Chesterfield | 0–2 | 4,022 | |
| 3 Apr 2026 | 2025–26 | League Two | A | Chesterfield | 0–1 | 8,072 |
See also: the Chesterfield archive and Chesterfield v Cheltenham Town.
All Cheltenham Town head-to-head records · Cheltenham Town season by season