| 25. Round | 01/01/2020 | AFC Wimbledon | - | Southend United | 1:1 | ||||
| 27. Round | 11/01/2020 | Southend United | - | Tranmere Rovers | 0:0 | ||||
| 28. Round | 18/01/2020 | Accrington Stanley | - | Southend United | 1:2 | ||||
| 30. Round | 28/01/2020 | Doncaster Rovers | - | Southend United | 3:1 | ||||
| 31. Round | 01/02/2020 | Southend United | - | Lincoln City | 2:1 | ||||
| 32. Round | 08/02/2020 | Blackpool FC | - | Southend United | 2:1 | ||||
| 34. Round | 15/02/2020 | Southend United | - | Coventry City | 0:2 | ||||
| 35. Round | 22/02/2020 | Southend United | - | Burton Albion | 2:3 | ||||
| 36. Round | 29/02/2020 | Oxford United | - | Southend United | 2:1 |
England