| League Two | 21/02/04 | Leyton Orient | - | Southend United | 2:1 |  |
|||
| League One | 26/09/08 | Southend United | - | Leyton Orient | 3:0 | ||||
| League One | 20/01/09 | Leyton Orient | - | Southend United | 1:1 | ||||
| League One | 04/09/09 | Southend United | - | Leyton Orient | 3:0 | ||||
| FA Cup | 10/11/18 | Southend United | - | Crawley Town | 1:1 | ||||
| FA Cup | 20/11/18 | Crawley Town | - | Southend United | 2:6 aet | ||||
| League Two | 03/10/20 | Crawley Town | - | Southend United | 1:1 | ||||
| League Two | 10/04/21 | Southend United | - | Crawley Town | 0:0 |
England