| 4. Round | 21/08/2018 | Luton Town | - | Southend United | 2:0 | ||||
| 6. Round | 01/09/2018 | Southend United | - | Charlton Athletic | 1:2 | ||||
| 7. Round | 08/09/2018 | Southend United | - | Peterborough United | 2:3 | ||||
| 8. Round | 15/09/2018 | Shrewsbury Town | - | Southend United | 2:0 | ||||
| 9. Round | 22/09/2018 | Southend United | - | Fleetwood Town | 1:0 | ||||
| 11. Round | 02/10/2018 | Burton Albion | - | Southend United | 1:2 | ||||
| 12. Round | 06/10/2018 | Southend United | - | Oxford United | 0:0 | ||||
| 13. Round | 13/10/2018 | Gillingham FC | - | Southend United | 0:2 | ||||
| 15. Round | 23/10/2018 | Southend United | - | Walsall FC | 3:0 | ||||
| 16. Round | 27/10/2018 | Sunderland AFC | - | Southend United | 3:0 | ||||
| 17. Round | 03/11/2018 | Barnsley FC | - | Southend United | 1:0 | ||||
| 18. Round | 17/11/2018 | Southend United | - | Blackpool FC | 1:2 | ||||
| 19. Round | 24/11/2018 | AFC Wimbledon | - | Southend United | 2:1 | ||||
| 20. Round | 27/11/2018 | Southend United | - | Scunthorpe United | 2:0 | ||||
| 23. Round | 22/12/2018 | Southend United | - | Rochdale AFC | 1:2 |
England