| 8. Round | 25/10/2019 | Sliema Wanderers | - | Mosta FC | 0:1 | ||||
| 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 | ||||
| 13. Round | 15/12/2019 | Sliema Wanderers | - | Floriana FC | 1:2 | ||||
| 14. Round | 11/01/2020 | Sliema Wanderers | - | Balzan FC | 1:2 | ||||
| 15. Round | 20/01/2020 | Valletta FC | - | Sliema Wanderers | 2:1 |
Italy