| League One | 14/01/06 | Southend United | - | Brentford FC | 4:1 | ||||
| League One | 14/02/06 | Brentford FC | - | Southend United | 2:0 | ||||
| League One | 11/08/07 | Southend United | - | Leyton Orient | 1:2 | ||||
| League One | 02/02/08 | Leyton Orient | - | Southend United | 2:2 | ||||
| League Two | 18/09/12 | Gillingham FC | - | Southend United | 1:0 | ||||
| League Two | 01/01/13 | Southend United | - | Gillingham FC | 0:1 | ||||
| League One | 24/10/15 | Gillingham FC | - | Southend United | 1:1 | ||||
| League One | 19/03/16 | Southend United | - | Gillingham FC | 1:1 | ||||
| League One | 06/08/16 | Southend United | - | Gillingham FC | 1:3 |  |
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| League Cup | 09/08/16 | Southend United | - | Gillingham FC | 1:3 | ||||
| League One | 25/02/17 | Gillingham FC | - | Southend United | 2:1 |
England