| 1. Round | 24/08/2019 | Gudja United | - | Hibernians FC | 1:1 | ||||
| 2. Round | 28/08/2019 | Hibernians FC | - | Tarxien Rainbows | 4:1 |  |
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| 3. Round | 14/09/2019 | Sirens FC | - | Hibernians FC | 2:1 | ||||
| 4. Round | 21/09/2019 | Hibernians FC | - | Senglea Athletics | 2:1 | |
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| 5. Round | 29/09/2019 | Mosta FC | - | Hibernians FC | 1:2 | |
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| 6. Round | 05/10/2019 | Hibernians FC | - | Birkirkara FC | 0:1 | ||||
| 7. Round | 21/10/2019 | Hibernians FC | - | Hamrun Spartans | 1:2 | ||||
| 8. Round | 28/10/2019 | St. Luċija FC | - | Hibernians FC | 0:2 | ||||
| 10. Round | 10/11/2019 | Floriana FC | - | Hibernians FC | 2:2 | ||||
| 11. Round | 24/11/2019 | Hibernians FC | - | Balzan FC | 2:1 | ||||
| 12. Round | 08/12/2019 | Valletta FC | - | Hibernians FC | 1:1 |  |
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| 13. Round | 13/12/2019 | Hibernians FC | - | Gżira United | 2:0 |
Netherlands