| League Cup | Matches | W | D | L |  |
 |
 |
| home | 1 | 1 | - | - | 2 | - | - |
| away | 1 | - | - | 1 | - | - | - |
| overall | 2 | 1 | - | 1 | 2 | - | - |
| Playoffs | Matches | W | D | L | |
|
|
| home | - | - | - | - | - | - | - |
| away | 1 | - | - | 1 | 3 | - | - |
| overall | 1 | - | - | 1 | 3 | - | - |
| League Cup | Home | - | Guest | |
|
|
Results |
| 11/08/98 | Southend United | - | Gillingham FC | 2 | - | - | 1:0 |
| 24/08/99 | Oxford United | - | Southend United | - | - | - | 1:0 |
| Playoffs | Home | - | Guest | |
|
|
Results |
| 16/05/08 | Doncaster Rovers | - | Southend United | 3 | - | - | 5:1 |
England