| 1. Round | 23/08/2019 | Sirens FC | - | Senglea Athletics | 1:1 | ||||
| 2. Round | 30/08/2019 | Mosta FC | - | Sirens FC | 3:4 | ||||
| 3. Round | 14/09/2019 | Sirens FC | - | Hibernians FC | 2:1 | ||||
| 4. Round | 21/09/2019 | Hamrun Spartans | - | Sirens FC | 4:0 | ||||
| 6. Round | 05/10/2019 | Sliema Wanderers | - | Sirens FC | 0:1 | ||||
| 7. Round | 19/10/2019 | Sirens FC | - | Floriana FC | 1:4 | ||||
| 11. Round | 23/11/2019 | Sirens FC | - | Gudja United | 1:1 | ||||
| 12. Round | 08/12/2019 | Tarxien Rainbows | - | Sirens FC | 0:3 | ||||
| 14. Round | 11/01/2020 | Senglea Athletics | - | Sirens FC | 2:2 |
Malta