| 26. Round | 26/01/2021 | Southend United | - | Bradford City | 1:3 |  |
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| 27. Round | 30/01/2021 | Port Vale FC | - | Southend United | 5:1 | ||||
| 22. Round | 09/02/2021 | Newport County | - | Southend United | 0:1 | ||||
| 33. Round | 02/03/2021 | Cheltenham Town | - | Southend United | 1:0 | ||||
| 34. Round | 06/03/2021 | Oldham Athletic | - | Southend United | 0:0 | ||||
| 35. Round | 09/03/2021 | Southend United | - | Tranmere Rovers | 0:2 | ||||
| 38. Round | 27/03/2021 | Harrogate Town | - | Southend United | 0:1 | ||||
| 39. Round | 03/04/2021 | Southend United | - | Carlisle United | 0:2 | ||||
| 40. Round | 06/04/2021 | Morecambe FC | - | Southend United | 1:1 | ||||
| 41. Round | 10/04/2021 | Southend United | - | Crawley Town | 0:0 | ||||
| 43. Round | 20/04/2021 | Colchester United | - | Southend United | 2:0 | |
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| 44. Round | 24/04/2021 | Southend United | - | Leyton Orient | 2:1 |  |
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| 45. Round | 01/05/2021 | Barrow AFC | - | Southend United | 1:2 | |
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| 46. Round | 08/05/2021 | Southend United | - | Newport County | 1:1 |
England