| League One | 26/08/17 | Gillingham FC | - | Southend United | 3:3 |  |
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| League One | 02/04/18 | Southend United | - | Gillingham FC | 4:0 | ||||
| League One | 01/01/19 | Southend United | - | Gillingham FC | 2:0 | ||||
| League One | 05/10/19 | Gillingham FC | - | Southend United | 3:1 | ||||
| League One | 18/02/20 | Southend United | - | Gillingham FC | 0:1 |  |
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| League Cup | 05/09/20 | Gillingham FC | - | Southend United | 1:0 | |
England