| League One | 08/10/16 | Rochdale AFC | - | Southend United | 3:0 |  |
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| League One | 14/02/17 | Oxford United | - | Southend United | 0:2 | ||||
| League One | 22/04/17 | Shrewsbury Town | - | Southend United | 1:0 | ||||
| League One | 23/10/18 | Plymouth Argyle | - | Gillingham FC | 3:1 |  |
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| FA Cup | 26/01/19 | Swansea City | - | Gillingham FC | 4:1 |
England