Cheltenham Town have played Chester 8 times in competitive football, winning 5, drawing 2 and losing 1, first meeting on 19 Oct 1999 and most recently on 18 Mar 2006. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 19 Oct 1999 | 1999–00 | Third Division | A | Chester | 1–2 | ||
| 29 Apr 2000 | 1999–00 | Third Division | H | Chester | 1–0 | ||
| 8 Oct 2004 | 2004–05 | League Two | H | Chester | 0–0 | ||
| 1 Feb 2005 | 2004–05 | League Two | A | Chester | 3–0 | ||
| 26 Dec 2005 | 2005–06 | League Two | H | Chester | 1–0 | ||
| 7 Jan 2006 | 2005–06 | FA Cup | H | Chester | 2–2 | ||
| 17 Jan 2006 | 2005–06 | FA Cup | A | Chester | 1–0 | ||
| 18 Mar 2006 | 2005–06 | League Two | A | Chester | 1–0 |
All Cheltenham Town head-to-head records · Cheltenham Town season by season