| 1. Journée | 03.08.2019 | Coventry City | - | Southend United | 1:0 |  |
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| 2. Journée | 10.08.2019 | Southend United | - | Blackpool FC | 1:3 | ||||
| 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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| 6. Journée | 31.08.2019 | Southend United | - | Rochdale AFC | 0:3 | ||||
| 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 | |
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| 13. Journée | 12.10.2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
| 15. Journée | 22.10.2019 | Southend United | - | Doncaster Rovers | 1:7 | |
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| 17. Journée | 02.11.2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
| 7. Journée | 05.11.2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 21. Journée | 14.12.2019 | Southend United | - | Rotherham United | 2:2 | ||||
| 22. Journée | 21.12.2019 | Bolton Wanderers | - | Southend United | 3:2 |  |
Angleterre