| 4. Round | 20/08/2019 | Portsmouth FC | - | Coventry City | 3:3 | ||||
| 6. Round | 31/08/2019 | Blackpool FC | - | Portsmouth FC | 1:1 |  |
|||
| 9. Round | 17/09/2019 | Portsmouth FC | - | Burton Albion | 2:2 | ||||
| 10. Round | 21/09/2019 | Wycombe Wanderers | - | Portsmouth FC | 1:0 | ||||
| 11. Round | 28/09/2019 | Portsmouth FC | - | Bolton Wanderers | 1:0 | ||||
| 7. Round | 05/11/2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 19. Round | 23/11/2019 | Rochdale AFC | - | Portsmouth FC | 0:3 | ||||
| 5. Round | 26/11/2019 | Portsmouth FC | - | Rotherham United | 3:2 | ||||
| 20. Round | 07/12/2019 | Portsmouth FC | - | Peterborough United | 2:2 | ||||
| 27. Round | 11/01/2020 | Portsmouth FC | - | AFC Wimbledon | 2:1 |
England