| 25. Journée | 01.01.2020 | AFC Wimbledon | - | Southend United | 1:1 | ||||
| 27. Journée | 11.01.2020 | Southend United | - | Tranmere Rovers | 0:0 | ||||
| 28. Journée | 18.01.2020 | Accrington Stanley | - | Southend United | 1:2 | ||||
| 30. Journée | 28.01.2020 | Doncaster Rovers | - | Southend United | 3:1 | ||||
| 31. Journée | 01.02.2020 | Southend United | - | Lincoln City | 2:1 | ||||
| 32. Journée | 08.02.2020 | Blackpool FC | - | Southend United | 2:1 | ||||
| 34. Journée | 15.02.2020 | Southend United | - | Coventry City | 0:2 | ||||
| 35. Journée | 22.02.2020 | Southend United | - | Burton Albion | 2:3 | ||||
| 36. Journée | 29.02.2020 | Oxford United | - | Southend United | 2:1 |
Angleterre