| League Two | 21.02.15 | Stevenage FC | - | Southend United | 4:2 |  |
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| Playoffs | 10.05.15 | Stevenage FC | - | Southend United | 1:1 | |
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| Playoffs | 14.05.15 | Southend United | - | Stevenage FC | 3:1 n.V. |  |
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| League One | 25.03.17 | AFC Wimbledon | - | Southend United | 0:2 | ||||
| League One | 26.09.17 | Southend United | - | AFC Wimbledon | 1:0 | ||||
| League One | 13.10.18 | Gillingham FC | - | Southend United | 0:2 | ||||
| League Cup | 13.08.19 | Stevenage FC | - | Southend United | 1:2 | |
England