| 2. Journée | 11.08.2018 | Plymouth Argyle | - | Southend United | 1:1 | ||||
| 3. Journée | 18.08.2018 | Southend United | - | Bradford City | 2:0 | ||||
| 5. Journée | 25.08.2018 | Bristol Rovers | - | Southend United | 0:1 | ||||
| 9. Journée | 22.09.2018 | Southend United | - | Fleetwood Town | 1:0 | ||||
| 11. Journée | 02.10.2018 | Burton Albion | - | Southend United | 1:2 | ||||
| 32. Journée | 09.02.2019 | Charlton Athletic | - | Southend United | 1:1 | ||||
| 27. Journée | 12.02.2019 | Doncaster Rovers | - | Southend United | 3:0 | ||||
| 33. Journée | 16.02.2019 | Southend United | - | Portsmouth FC | 3:3 |  |
|||
| 34. Journée | 23.02.2019 | Accrington Stanley | - | Southend United | 1:1 | |
|||
| 35. Journée | 02.03.2019 | Southend United | - | Barnsley FC | 0:3 |
Angleterre