1. Round | 24/08/2019 | Gudja United | - | Hibernians FC | 1:1 | ||||
2. Round | 30/08/2019 | Hamrun Spartans | - | Gudja United | 2:2 | ||||
6. Round | 05/10/2019 | Balzan FC | - | Gudja United | 1:0 | ||||
7. Round | 20/10/2019 | Gudja United | - | Valletta FC | 0:1 | ||||
8. Round | 26/10/2019 | Gżira United | - | Gudja United | 6:1 | ||||
9. Round | 04/11/2019 | Birkirkara FC | - | Gudja United | 2:3 | ||||
11. Round | 23/11/2019 | Sirens FC | - | Gudja United | 1:1 | ||||
12. Round | 07/12/2019 | Gudja United | - | Senglea Athletics | 4:1 | ||||
13. Round | 08/01/2020 | Mosta FC | - | Gudja United | 1:0 | ||||
14. Round | 12/01/2020 | Hibernians FC | - | Gudja United | 2:0 |