Chelsea have played Southend United 4 times in competitive football, winning 3, drawing 1 and losing 0, first meeting on 11 Jan 1913 and most recently on 14 Jan 2009. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 11 Jan 1913 | 1912–13 | FA Cup | H | Southend United | 5–2 | ||
| 6 Sep 1972 | 1972–73 | League Cup | A | Southend United | 1–0 | ||
| 3 Jan 2009 | 2008–09 | FA Cup | H | Southend United | 1–1 | Salomon Kalou 31 | 41,090 |
| 14 Jan 2009 | 2008–09 | FA Cup | A | Southend United | 4–1 | Michael Ballack 45, Salomon Kalou 60, Nicolas Anelka 78, Frank Lampard 90 | 11,314 |