Chelsea have played York City 5 times in competitive football, winning 2, drawing 2 and losing 1, first meeting on 4 Oct 1975 and most recently on 8 Oct 1986. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 4 Oct 1975 | 1975–76 | Second Division | H | York City | 0–0 | ||
| 24 Jan 1976 | 1975–76 | FA Cup | A | York City | 2–0 | ||
| 24 Apr 1976 | 1975–76 | Second Division | A | York City | 2–2 | ||
| 23 Sep 1986 | 1986–87 | League Cup | A | York City | 0–1 | ||
| 8 Oct 1986 | 1986–87 | League Cup | H | York City | 3–0 |