| Gruppe B | 03.09.2019 | Portsmouth FC | - | Crawley Town | 1:0 | ||||
| Gruppe B | 14.09.2019 | Portsmouth FC | - | Norwich City U23 | 3:1 |  |
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| Gruppe B | 08.10.2019 | Oxford United | - | Portsmouth FC | 4:5 i.E. | ||||
| Achtelfinale | 07.01.2020 | Walsall FC | - | Portsmouth FC | 1:2 | |
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| Halbfinale | 18.02.2020 | Portsmouth FC | - | Exeter City | 3:2 |
Wales