| 1. Round | 03/08/2019 | Shrewsbury Town | - | Portsmouth FC | 1:0 |  |
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| 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 |  |
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| 9. Round | 17/09/2019 | Portsmouth FC | - | Burton Albion | 2:2 | ||||
| 15. Round | 22/10/2019 | Portsmouth FC | - | Lincoln City | 1:0 | ||||
| 16. Round | 26/10/2019 | Bristol Rovers | - | Portsmouth FC | 2:2 | |
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| 17. Round | 02/11/2019 | Portsmouth FC | - | Oxford United | 1:1 | |
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| 7. Round | 05/11/2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 20. Round | 07/12/2019 | Portsmouth FC | - | Peterborough United | 2:2 | ||||
| 21. Round | 14/12/2019 | Accrington Stanley | - | Portsmouth FC | 4:1 | |
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| 22. Round | 21/12/2019 | Portsmouth FC | - | Ipswich Town | 1:0 | ||||
| 34. Round | 15/02/2020 | Portsmouth FC | - | Shrewsbury Town | 2:0 | ||||
| 35. Round | 22/02/2020 | Fleetwood Town | - | Portsmouth FC | 1:0 | ||||
| 29. Round | 25/02/2020 | Portsmouth FC | - | Milton Keynes Dons | 3:1 | ||||
| 37. Round | 07/03/2020 | Peterborough United | - | Portsmouth FC | 2:0 | ||||
| 18. Round | 10/03/2020 | Portsmouth FC | - | Fleetwood Town | 2:2 |
Scotland