| FA Cup | M. | W | D | L | goals | |||
| at home | 1 | 0 | 0 | 1 | 1 | : | 4 | |
| Away | 2 | 0 | 1 | 1 | 3 | : | 6 | |
| ∑ | 3 | 0 | 1 | 2 | 4 | : | 10 | |
| League Cup | M. | W | D | L | goals | |||
| at home | 1 | 0 | 0 | 1 | 0 | : | 1 | |
| ∑ | 1 | 0 | 0 | 1 | 0 | : | 1 | |
| overall | M. | W | D | L | goals | |||
| at home | 2 | 0 | 0 | 2 | 1 | : | 5 | |
| Away | 2 | 0 | 1 | 1 | 3 | : | 6 | |
| Neutral Place | 0 | 0 | 0 | 0 | 0 | : | 0 | |
| ∑ | 4 | 0 | 1 | 3 | 4 | : | 11 | |
| FA Cup | |||||
| 2008/2009 | 3. Round | Southend United | - | Chelsea FC | 1:4 (1:1) |
| 2008/2009 | 3. Round | Chelsea FC | - | Southend United | 1:1 (1:0) |
| 1912/1913 | 1. Round | Chelsea FC | - | Southend United | 5:2 |
| League Cup | |||||
| 1972/1973 | 2. Round | Southend United | - | Chelsea FC | 0:1 |
|
For games that were decided on penalties the score after 120 minutes will be included in the ranking |
England 
![Southend United [U18]](https://s.hs-data.com/bilder/wappen/mini/33329.gif?fallback=png "Southend United [U18]"){kind=small}
