| 31. Round | 01/02/2020 | Southend United | - | Lincoln City | 2:1 | ||||
| 32. Round | 08/02/2020 | Blackpool FC | - | Southend United | 2:1 | ||||
| 33. Round | 11/02/2020 | Peterborough United | - | Southend United | 4:0 | ||||
| 34. Round | 15/02/2020 | Southend United | - | Coventry City | 0:2 | ||||
| 26. Round | 18/02/2020 | Southend United | - | Gillingham FC | 0:1 | ||||
| 35. Round | 22/02/2020 | Southend United | - | Burton Albion | 2:3 | ||||
| 36. Round | 29/02/2020 | Oxford United | - | Southend United | 2:1 | ||||
| 37. Round | 07/03/2020 | Southend United | - | Bristol Rovers | 3:1 |
England