Chelsea have played Gainsborough Trinity 8 times in competitive football, winning 5, drawing 1 and losing 2, first meeting on 16 Dec 1905 and most recently on 20 Mar 1912. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 16 Dec 1905 | 1905–06 | Second Division | A | Gainsborough Trinity | 2–0 | J. Robertson 20, Hall 2nd | 8,000 |
| 21 Apr 1906 | 1905–06 | Second Division | H | Gainsborough Trinity | 1–3 | ||
| 22 Dec 1906 | 1906–07 | Second Division | A | Gainsborough Trinity | 1–1 | ||
| 27 Apr 1907 | 1906–07 | Second Division | H | Gainsborough Trinity | 4–1 | ||
| 24 Dec 1910 | 1910–11 | Second Division | H | Gainsborough Trinity | 3–0 | ||
| 29 Apr 1911 | 1910–11 | Second Division | A | Gainsborough Trinity | 1–3 | ||
| 30 Sep 1911 | 1911–12 | Second Division | H | Gainsborough Trinity | 1–0 | ||
| 20 Mar 1912 | 1911–12 | Second Division | A | Gainsborough Trinity | 2–0 |