| 1. Round | 12/09/2020 | Southend United | - | Harrogate Town | 0:4 |  |
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| 2. Round | 19/09/2020 | Carlisle United | - | Southend United | 2:0 | ||||
| 3. Round | 26/09/2020 | Southend United | - | Morecambe FC | 1:2 | |
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| 4. Round | 03/10/2020 | Crawley Town | - | Southend United | 1:1 | ||||
| 7. Round | 20/10/2020 | Salford City | - | Southend United | 3:0 | |
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| 15. Round | 28/11/2020 | Bolton Wanderers | - | Southend United | 3:0 | ||||
| 16. Round | 05/12/2020 | Stevenage FC | - | Southend United | 0:0 | |
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| 17. Round | 12/12/2020 | Southend United | - | Scunthorpe United | 1:0 | ||||
| 19. Round | 19/12/2020 | Mansfield Town | - | Southend United | 1:1 | |
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| 21. Round | 29/12/2020 | Leyton Orient | - | Southend United | 2:0 | ||||
| 23. Round | 09/01/2021 | Southend United | - | Barrow AFC | 1:0 | ||||
| 26. Round | 26/01/2021 | Southend United | - | Bradford City | 1:3 |
England
Nigeria