1. Round | 21/08/2021 | King's Lynn | - | Southend United | 0:1 | ||||
2. Round | 28/08/2021 | Southend United | - | Stockport County | 0:1 | ||||
3. Round | 30/08/2021 | Wealdstone FC | - | Southend United | 0:0 | ||||
4. Round | 04/09/2021 | Southend United | - | Wrexham AFC | 2:2 | ||||
5. Round | 11/09/2021 | Halifax Town | - | Southend United | 3:1 | ||||
12. Round | 23/10/2021 | Dagenham & Redbridge | - | Southend United | 3:0 | ||||
13. Round | 02/11/2021 | Southend United | - | Dover Athletic | 4:1 | ||||
15. Round | 13/11/2021 | Southend United | - | Woking FC | 0:2 | ||||
18. Round | 27/11/2021 | Altrincham FC | - | Southend United | 1:2 |