| 1. Round | 24/08/2019 | Gudja United | - | Hibernians FC | 1:1 | ||||
| 2. Round | 30/08/2019 | Hamrun Spartans | - | Gudja United | 2:2 | ||||
| 3. Round | 15/09/2019 | Gudja United | - | St. Luċija FC | 1:1 |  |
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| 4. Round | 21/09/2019 | Sliema Wanderers | - | Gudja United | 1:1 | ||||
| 5. Round | 28/09/2019 | Gudja United | - | Floriana FC | 0:2 |  |
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| 7. Round | 20/10/2019 | Gudja United | - | Valletta FC | 0:1 | ||||
| 8. Round | 26/10/2019 | Gżira United | - | Gudja United | 6:1 | ||||
| 10. Round | 09/11/2019 | Gudja United | - | Tarxien Rainbows | 3:2 |
Brazil