| 4. Round | 03/10/2020 | Crawley Town | - | Southend United | 1:1 | ||||
| 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 |  |
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| 8. Round | 24/10/2020 | Tranmere Rovers | - | Southend United | 2:0 | ||||
| 9. Round | 27/10/2020 | Southend United | - | Oldham Athletic | 1:2 | ||||
| 10. Round | 31/10/2020 | Southend United | - | Port Vale FC | 0:2 | |
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| 11. Round | 03/11/2020 | Bradford City | - | Southend United | 3:0 | ||||
| 12. Round | 14/11/2020 | Walsall FC | - | Southend United | 0:1 | |
England