| 13. Round | 12/10/2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
| 14. Round | 18/10/2019 | Tranmere Rovers | - | Southend United | 1:1 |  |
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| 15. Round | 22/10/2019 | Southend United | - | Doncaster Rovers | 1:7 | ||||
| 16. Round | 26/10/2019 | Southend United | - | Ipswich Town | 1:3 | ||||
| 17. Round | 02/11/2019 | Sunderland AFC | - | Southend United | 1:0 |  |
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| 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 | |
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| 22. Round | 21/12/2019 | Bolton Wanderers | - | Southend United | 3:2 | ||||
| 23. Round | 26/12/2019 | Southend United | - | Milton Keynes Dons | 2:2 | ||||
| 25. Round | 01/01/2020 | AFC Wimbledon | - | Southend United | 1:1 | |
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| 27. Round | 11/01/2020 | Southend United | - | Tranmere Rovers | 0:0 | ||||
| 28. Round | 18/01/2020 | Accrington Stanley | - | Southend United | 1:2 |
England
