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 | ||||
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 |