2. Round | 28/08/2021 | Southend United | - | Stockport County | 0:1 | ||||
3. Round | 30/08/2021 | Wealdstone FC | - | Southend United | 0:0 | ||||
7. Round | 18/09/2021 | Torquay United | - | Southend United | 1:0 | ||||
10. Round | 05/10/2021 | Southend United | - | Eastleigh FC | 1:0 | ||||
11. Round | 09/10/2021 | Southend United | - | Chesterfield FC | 0:4 |