| League One | 24/10/15 | Gillingham FC | - | Southend United | 1:1 |  |
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| League One | 19/03/16 | Southend United | - | Gillingham FC | 1:1 | |
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| League One | 06/08/16 | Southend United | - | Gillingham FC | 1:3 | ||||
| League Cup | 09/08/16 | Southend United | - | Gillingham FC | 1:3 | ||||
| League One | 25/02/17 | Gillingham FC | - | Southend United | 2:1 | ||||
| League One | 02/04/18 | Southend United | - | Gillingham FC | 4:0 | ||||
| League One | 13/10/18 | Gillingham FC | - | Southend United | 0:2 |
England