| 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 | ||||
| 6. Round | 31/08/2019 | Southend United | - | Rochdale AFC | 0:3 |  |
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| 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 | ||||
| 13. Round | 12/10/2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
| 14. Round | 18/10/2019 | Tranmere Rovers | - | Southend United | 1:1 | ||||
| 15. Round | 22/10/2019 | Southend United | - | Doncaster Rovers | 1:7 |  |
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| 19. Round | 23/11/2019 | Southend United | - | Oxford United | 0:4 | ||||
| 20. Round | 07/12/2019 | Bristol Rovers | - | Southend United | 4:2 |
Scotland