1. Round | 03/08/2019 | Shrewsbury Town | - | Portsmouth FC | 1:0 | ||||
2. Round | 10/08/2019 | Portsmouth FC | - | Tranmere Rovers | 2:0 | ||||
3. Round | 17/08/2019 | Sunderland AFC | - | Portsmouth FC | 2:1 | ||||
6. Round | 31/08/2019 | Blackpool FC | - | Portsmouth FC | 1:1 | ||||
19. Round | 23/11/2019 | Rochdale AFC | - | Portsmouth FC | 0:3 | ||||
5. Round | 26/11/2019 | Portsmouth FC | - | Rotherham United | 3:2 | ||||
21. Round | 14/12/2019 | Accrington Stanley | - | Portsmouth FC | 4:1 | ||||
22. Round | 21/12/2019 | Portsmouth FC | - | Ipswich Town | 1:0 | ||||
23. Round | 26/12/2019 | Portsmouth FC | - | Wycombe Wanderers | 2:0 | ||||
24. Round | 29/12/2019 | Milton Keynes Dons | - | Portsmouth FC | 3:1 | ||||
25. Round | 01/01/2020 | Gillingham FC | - | Portsmouth FC | 1:1 |