| 17. Ronde | 02.11.2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
| 7. Ronde | 05.11.2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 22. Ronde | 21.12.2019 | Bolton Wanderers | - | Southend United | 3:2 | ||||
| 32. Ronde | 08.02.2020 | Blackpool FC | - | Southend United | 2:1 | ||||
| 33. Ronde | 11.02.2020 | Peterborough United | - | Southend United | 4:0 | ||||
| 26. Ronde | 18.02.2020 | Southend United | - | Gillingham FC | 0:1 | ||||
| 37. Ronde | 07.03.2020 | Southend United | - | Bristol Rovers | 3:1 |
Engeland