| League Two | 03/10/20 | Crawley Town | - | Southend United | 1:1 | ||||
| Nat. League | 12/02/22 | Woking FC | - | Southend United | 2:3 | ||||
| Nat. League | 24/09/22 | Wealdstone FC | - | Southend United | 0:1 | ||||
| Nat. League | 29/04/23 | Southend United | - | Wealdstone FC | 2:1 | ||||
| Nat. League | 05/03/24 | Southend United | - | Wealdstone FC | 1:1 | ||||
| Nat. League | 09/04/24 | Wealdstone FC | - | Southend United | 1:2 | ||||
| Nat. League | 19/10/24 | Rochdale AFC | - | Southend United | 0:1 |  |
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| Nat. League | 15/02/25 | Southend United | - | Rochdale AFC | 1:1 | ||||
| Playoffs | 15/05/25 | Rochdale AFC | - | Southend United | 3:4 aet |
England