| 3. Round | 14/09/2019 | Senglea Athletics | - | Mosta FC | 2:1 | ||||
| 7. Round | 18/10/2019 | Senglea Athletics | - | Sliema Wanderers | 2:0 | ||||
| 8. Round | 25/10/2019 | Floriana FC | - | Senglea Athletics | 5:0 |  |
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| 11. Round | 25/11/2019 | Senglea Athletics | - | Gżira United | 1:3 | ||||
| 12. Round | 07/12/2019 | Gudja United | - | Senglea Athletics | 4:1 | ||||
| 17. Round | 09/02/2020 | Senglea Athletics | - | Hibernians FC | 1:1 | ||||
| 18. Round | 17/02/2020 | Hamrun Spartans | - | Senglea Athletics | 1:0 | ||||
| 19. Round | 22/02/2020 | Senglea Athletics | - | St. Luċija FC | 2:5 | ||||
| 20. Round | 07/03/2020 | Sliema Wanderers | - | Senglea Athletics | 4:1 |
Australia