| 3. Round | 14/09/2019 | Gżira United | - | Sliema Wanderers | 1:1 | ||||
| 6. Round | 05/10/2019 | Sliema Wanderers | - | Sirens FC | 0:1 | ||||
| 7. Round | 18/10/2019 | Senglea Athletics | - | Sliema Wanderers | 2:0 | ||||
| 9. Round | 03/11/2019 | Hibernians FC | - | Sliema Wanderers | 1:0 | ||||
| 10. Round | 08/11/2019 | Sliema Wanderers | - | Hamrun Spartans | 2:0 | ||||
| 11. Round | 23/11/2019 | St. Luċija FC | - | Sliema Wanderers | 0:4 | ||||
| 12. Round | 07/12/2019 | Sliema Wanderers | - | Birkirkara FC | 2:1 | ||||
| 13. Round | 15/12/2019 | Sliema Wanderers | - | Floriana FC | 1:2 |  |
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| 14. Round | 11/01/2020 | Sliema Wanderers | - | Balzan FC | 1:2 | |
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| 15. Round | 20/01/2020 | Valletta FC | - | Sliema Wanderers | 2:1 | ||||
| 16. Round | 01/02/2020 | Sliema Wanderers | - | Gżira United | 2:0 |  |
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| 17. Round | 08/02/2020 | Gudja United | - | Sliema Wanderers | 1:0 | ||||
| 18. Round | 15/02/2020 | Sliema Wanderers | - | Tarxien Rainbows | 1:0 | ||||
| 19. Round | 21/02/2020 | Sirens FC | - | Sliema Wanderers | 0:0 | ||||
| 20. Round | 07/03/2020 | Sliema Wanderers | - | Senglea Athletics | 4:1 | |
Malta