| 3. Round | 17/08/2019 | Lincoln City | - | Southend United | 4:0 | ||||
| 4. Round | 20/08/2019 | Southend United | - | Peterborough United | 0:2 | ||||
| 5. Round | 24/08/2019 | Wycombe Wanderers | - | Southend United | 4:3 |  |
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| 14. Round | 18/10/2019 | Tranmere Rovers | - | Southend United | 1:1 | ||||
| 15. Round | 22/10/2019 | Southend United | - | Doncaster Rovers | 1:7 | ||||
| 17. Round | 02/11/2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
| 7. Round | 05/11/2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 19. Round | 23/11/2019 | Southend United | - | Oxford United | 0:4 | ||||
| 18. Round | 03/12/2019 | Burton Albion | - | Southend United | 1:1 | ||||
| 20. Round | 07/12/2019 | Bristol Rovers | - | Southend United | 4:2 | ||||
| 21. Round | 14/12/2019 | Southend United | - | Rotherham United | 2:2 | ||||
| 22. Round | 21/12/2019 | Bolton Wanderers | - | Southend United | 3:2 |
England