Sheffield Wednesday have played Chester 16 times in competitive football, winning 5, drawing 7 and losing 4, first meeting on 21 Jan 1939 and most recently on 29 Sep 2004. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 21 Jan 1939 | 1938–39 | FA Cup | H | Chester | 1–1 | ||
| 25 Jan 1939 | 1938–39 | FA Cup | A | Chester | 1–1 | ||
| 30 Jan 1939 | 1938–39 | FA Cup | H | Chester | 2–0 | ||
| 21 Oct 1975 | 1975–76 | Third Division | A | Chester | 0–1 | ||
| 31 Jan 1976 | 1975–76 | Third Division | H | Chester | 2–0 | ||
| 5 Oct 1976 | 1976–77 | Third Division | H | Chester | 3–0 | ||
| 15 Feb 1977 | 1976–77 | Third Division | A | Chester | 0–1 | ||
| 14 Sep 1977 | 1977–78 | Third Division | A | Chester | 1–2 | ||
| 7 Mar 1978 | 1977–78 | Third Division | H | Chester | 1–1 | ||
| 9 Dec 1978 | 1978–79 | Third Division | H | Chester | 0–0 | ||
| 28 Apr 1979 | 1978–79 | Third Division | A | Chester | 2–2 | ||
| 1 Dec 1979 | 1979–80 | Third Division | A | Chester | 2–2 | ||
| 19 Apr 1980 | 1979–80 | Third Division | H | Chester | 3–0 | ||
| 31 Jan 1987 | 1986–87 | FA Cup | A | Chester | 1–1 | ||
| 4 Feb 1987 | 1986–87 | FA Cup | H | Chester | 3–1 | ||
| 29 Sep 2004 | 2004–05 | EFL Trophy | H | Chester | 1–2 | Steve MacLean | 7,640 |
All Sheffield Wednesday head-to-head records · Sheffield Wednesday season by season