| 3. Journée | 17.08.2019 | Lincoln City | - | Southend United | 4:0 | ||||
| 4. Journée | 20.08.2019 | Southend United | - | Peterborough United | 0:2 | ||||
| 5. Journée | 24.08.2019 | Wycombe Wanderers | - | Southend United | 4:3 |  |
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| 14. Journée | 18.10.2019 | Tranmere Rovers | - | Southend United | 1:1 | ||||
| 15. Journée | 22.10.2019 | Southend United | - | Doncaster Rovers | 1:7 | ||||
| 17. Journée | 02.11.2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
| 7. Journée | 05.11.2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 19. Journée | 23.11.2019 | Southend United | - | Oxford United | 0:4 | ||||
| 18. Journée | 03.12.2019 | Burton Albion | - | Southend United | 1:1 | ||||
| 20. Journée | 07.12.2019 | Bristol Rovers | - | Southend United | 4:2 | ||||
| 21. Journée | 14.12.2019 | Southend United | - | Rotherham United | 2:2 | ||||
| 22. Journée | 21.12.2019 | Bolton Wanderers | - | Southend United | 3:2 |
Angleterre