| 1. Round | 23/08/2019 | Sirens FC | - | Senglea Athletics | 1:1 | ||||
| 2. Round | 28/08/2019 | Senglea Athletics | - | Birkirkara FC | 1:0 | ||||
| 3. Round | 14/09/2019 | Senglea Athletics | - | Mosta FC | 2:1 |  |
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| 4. Round | 21/09/2019 | Hibernians FC | - | Senglea Athletics | 2:1 | ||||
| 5. Round | 28/09/2019 | Senglea Athletics | - | Hamrun Spartans | 1:3 | ||||
| 6. Round | 05/10/2019 | St. Luċija FC | - | Senglea Athletics | 0:0 | ||||
| 7. Round | 18/10/2019 | Senglea Athletics | - | Sliema Wanderers | 2:0 | |
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| 8. Round | 25/10/2019 | Floriana FC | - | Senglea Athletics | 5:0 | ||||
| 9. Round | 02/11/2019 | Senglea Athletics | - | Balzan FC | 2:2 | ||||
| 10. Round | 08/11/2019 | Valletta FC | - | Senglea Athletics | 1:0 | ||||
| 11. Round | 25/11/2019 | Senglea Athletics | - | Gżira United | 1:3 | ||||
| 12. Round | 07/12/2019 | Gudja United | - | Senglea Athletics | 4:1 | ||||
| 13. Round | 16/12/2019 | Senglea Athletics | - | Tarxien Rainbows | 2:2 | ||||
| 16. Round | 01/02/2020 | Mosta FC | - | 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 |  |
Japan