| League Two | 21.02.04 | Leyton Orient | - | Southend United | 2:1 |  |
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| 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 ap | ||||
| League Two | 03.10.20 | Crawley Town | - | Southend United | 1:1 | ||||
| League Two | 10.04.21 | Southend United | - | Crawley Town | 0:0 |
Angleterre