| 1. Round | 03/08/2019 | Coventry City | - | Southend United | 1:0 |  |
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| 2. Round | 10/08/2019 | Southend United | - | Blackpool FC | 1:3 | ||||
| 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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| 6. Round | 31/08/2019 | Southend United | - | Rochdale AFC | 0:3 | ||||
| 8. Round | 14/09/2019 | Southend United | - | Fleetwood Town | 3:3 | ||||
| 9. Round | 17/09/2019 | Shrewsbury Town | - | Southend United | 4:3 | ||||
| 10. Round | 21/09/2019 | Milton Keynes Dons | - | Southend United | 0:1 | |
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| 11. Round | 28/09/2019 | Southend United | - | Accrington Stanley | 0:1 | ||||
| 12. Round | 05/10/2019 | Gillingham FC | - | Southend United | 3:1 | |
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| 13. Round | 12/10/2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
| 15. Round | 22/10/2019 | Southend United | - | Doncaster Rovers | 1:7 | |
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| 17. Round | 02/11/2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
| 7. Round | 05/11/2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 21. Round | 14/12/2019 | Southend United | - | Rotherham United | 2:2 | ||||
| 22. Round | 21/12/2019 | Bolton Wanderers | - | Southend United | 3:2 |  |
England