| Gruppe B | 03.09.2019 | Portsmouth FC | - | Crawley Town | 1:0 | ||||
| Gruppe B | 08.10.2019 | Oxford United | - | Portsmouth FC | 4:5 i.E. | ||||
| 2. Runde | 03.12.2019 | Portsmouth FC | - | Northampton Town | 2:1 | ||||
| Achtelfinale | 07.01.2020 | Walsall FC | - | Portsmouth FC | 1:2 | ||||
| Viertelfinale | 21.01.2020 | Portsmouth FC | - | Scunthorpe United | 2:1 |
England