| 1. Jornada | 04.08.2018 | Southend United | - | Doncaster Rovers | 2:3 | ||||
| 2. Jornada | 11.08.2018 | Plymouth Argyle | - | Southend United | 1:1 | ||||
| 3. Jornada | 18.08.2018 | Southend United | - | Bradford City | 2:0 | ||||
| 4. Jornada | 21.08.2018 | Luton Town | - | Southend United | 2:0 | ||||
| 5. Jornada | 25.08.2018 | Bristol Rovers | - | Southend United | 0:1 |  |
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| 6. Jornada | 01.09.2018 | Southend United | - | Charlton Athletic | 1:2 | ||||
| 7. Jornada | 08.09.2018 | Southend United | - | Peterborough United | 2:3 | ||||
| 8. Jornada | 15.09.2018 | Shrewsbury Town | - | Southend United | 2:0 | ||||
| 9. Jornada | 22.09.2018 | Southend United | - | Fleetwood Town | 1:0 | ||||
| 10. Jornada | 29.09.2018 | Wycombe Wanderers | - | Southend United | 2:3 | ||||
| 11. Jornada | 02.10.2018 | Burton Albion | - | Southend United | 1:2 | ||||
| 12. Jornada | 06.10.2018 | Southend United | - | Oxford United | 0:0 | ||||
| 13. Jornada | 13.10.2018 | Gillingham FC | - | Southend United | 0:2 | ||||
| 14. Jornada | 20.10.2018 | Southend United | - | Coventry City | 1:2 | |
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| 15. Jornada | 23.10.2018 | Southend United | - | Walsall FC | 3:0 | ||||
| 16. Jornada | 27.10.2018 | Sunderland | - | Southend United | 3:0 |
Inglaterra