| 1. Round | 24/08/2019 | Gudja United | - | Hibernians FC | 1:1 | ||||
| 2. Round | 28/08/2019 | Hibernians FC | - | Tarxien Rainbows | 4:1 | ||||
| 3. Round | 14/09/2019 | Sirens FC | - | Hibernians FC | 2:1 | ||||
| 4. Round | 21/09/2019 | Hibernians FC | - | Senglea Athletics | 2:1 | ||||
| 5. Round | 29/09/2019 | Mosta FC | - | Hibernians FC | 1:2 | ||||
| 6. Round | 05/10/2019 | Hibernians FC | - | Birkirkara FC | 0:1 | ||||
| 7. Round | 21/10/2019 | Hibernians FC | - | Hamrun Spartans | 1:2 | ||||
| 14. Round | 12/01/2020 | Hibernians FC | - | Gudja United | 2:0 |
Ghana
Italy