Chelsea have played Scarborough 3 times in competitive football, winning 1, drawing 1 and losing 1, first meeting on 19 Sep 1989 and most recently on 24 Jan 2004. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 19 Sep 1989 | 1989–90 | League Cup | H | Scarborough | 1–1 | ||
| 4 Oct 1989 | 1989–90 | League Cup | A | Scarborough | 2–3 | ||
| 24 Jan 2004 | 2003–04 | FA Cup | A | Scarborough | 1–0 | John Terry 10 | 5,379 |