| 1. Round | 24/08/2019 | Balzan FC | - | Sliema Wanderers | 2:1 |  |
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| 2. Round | 29/08/2019 | Sliema Wanderers | - | Valletta FC | 1:3 | ||||
| 3. Round | 14/09/2019 | Gżira United | - | Sliema Wanderers | 1:1 | ||||
| 4. Round | 21/09/2019 | Sliema Wanderers | - | Gudja United | 1:1 | ||||
| 5. Round | 27/09/2019 | Tarxien Rainbows | - | Sliema Wanderers | 1:2 | ||||
| 6. Round | 05/10/2019 | Sliema Wanderers | - | Sirens FC | 0:1 | ||||
| 7. Round | 18/10/2019 | Senglea Athletics | - | Sliema Wanderers | 2:0 | ||||
| 12. Round | 07/12/2019 | Sliema Wanderers | - | Birkirkara FC | 2:1 | |
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| 13. Round | 15/12/2019 | Sliema Wanderers | - | Floriana FC | 1:2 | ||||
| 16. Round | 01/02/2020 | Sliema Wanderers | - | Gżira United | 2:0 | ||||
| 17. Round | 08/02/2020 | Gudja United | - | Sliema Wanderers | 1:0 | ||||
| 20. Round | 07/03/2020 | Sliema Wanderers | - | Senglea Athletics | 4:1 |  |
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Italy