| 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 | ||||
| 6. Journée | 31.08.2019 | Southend United | - | Rochdale AFC | 0:3 |  |
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| 8. Journée | 14.09.2019 | Southend United | - | Fleetwood Town | 3:3 | ||||
| 9. Journée | 17.09.2019 | Shrewsbury Town | - | Southend United | 4:3 | ||||
| 10. Journée | 21.09.2019 | Milton Keynes Dons | - | Southend United | 0:1 | |
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| 11. Journée | 28.09.2019 | Southend United | - | Accrington Stanley | 0:1 | ||||
| 12. Journée | 05.10.2019 | Gillingham FC | - | Southend United | 3:1 | ||||
| 13. Journée | 12.10.2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
| 14. Journée | 18.10.2019 | Tranmere Rovers | - | Southend United | 1:1 | ||||
| 15. Journée | 22.10.2019 | Southend United | - | Doncaster Rovers | 1:7 |  |
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| 19. Journée | 23.11.2019 | Southend United | - | Oxford United | 0:4 | ||||
| 20. Journée | 07.12.2019 | Bristol Rovers | - | Southend United | 4:2 |
Écosse