| 1. Round | 12/09/2020 | Southend United | - | Harrogate Town | 0:4 | ||||
| 2. Round | 19/09/2020 | Carlisle United | - | Southend United | 2:0 | ||||
| 3. Round | 26/09/2020 | Southend United | - | Morecambe FC | 1:2 | ||||
| 4. Round | 03/10/2020 | Crawley Town | - | Southend United | 1:1 |  |
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| 5. Round | 10/10/2020 | Southend United | - | Exeter City | 2:2 | ||||
| 6. Round | 17/10/2020 | Southend United | - | Cheltenham Town | 0:2 | ||||
| 7. Round | 20/10/2020 | Salford City | - | Southend United | 3:0 |
England