| 13. Jornada | 12.10.2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
| 14. Jornada | 18.10.2019 | Tranmere Rovers | - | Southend United | 1:1 |  |
|||
| 15. Jornada | 22.10.2019 | Southend United | - | Doncaster Rovers | 1:7 | ||||
| 16. Jornada | 26.10.2019 | Southend United | - | Ipswich Town | 1:3 | ||||
| 17. Jornada | 02.11.2019 | Sunderland | - | Southend United | 1:0 |  |
|||
| 7. Jornada | 05.11.2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 19. Jornada | 23.11.2019 | Southend United | - | Oxford United | 0:4 | ||||
| 18. Jornada | 03.12.2019 | Burton Albion | - | Southend United | 1:1 | ||||
| 20. Jornada | 07.12.2019 | Bristol Rovers | - | Southend United | 4:2 | |
|||
| 22. Jornada | 21.12.2019 | Bolton Wanderers | - | Southend United | 3:2 | ||||
| 23. Jornada | 26.12.2019 | Southend United | - | Milton Keynes Dons | 2:2 | ||||
| 25. Jornada | 01.01.2020 | AFC Wimbledon | - | Southend United | 1:1 | |
|||
| 27. Jornada | 11.01.2020 | Southend United | - | Tranmere Rovers | 0:0 | ||||
| 28. Jornada | 18.01.2020 | Accrington Stanley | - | Southend United | 1:2 |
Inglaterra