| 2. Round | 24/08/2018 | St. Andrews FC | - | Tarxien Rainbows | 1:5 | ||||
| 5. Round | 28/09/2018 | Hibernians FC | - | St. Andrews FC | 2:0 |  |
|||
| 7. Round | 19/10/2018 | Qormi FC | - | St. Andrews FC | 0:2 | ||||
| 10. Round | 10/11/2018 | St. Andrews FC | - | Pietá Hotspurs | 3:3 | ||||
| 15. Round | 19/01/2019 | Tarxien Rainbows | - | St. Andrews FC | 2:1 | ||||
| 16. Round | 02/02/2019 | St. Andrews FC | - | Hamrun Spartans | 0:3 | ||||
| 17. Round | 09/02/2019 | Sliema Wanderers | - | St. Andrews FC | 1:1 | |
|||
| 18. Round | 16/02/2019 | St. Andrews FC | - | Hibernians FC | 1:2 | ||||
| 19. Round | 02/03/2019 | Birkirkara FC | - | St. Andrews FC | 2:0 | |
|||
| 20. Round | 09/03/2019 | St. Andrews FC | - | Qormi FC | 0:2 | ||||
| 23. Round | 07/04/2019 | Pietá Hotspurs | - | St. Andrews FC | 3:1 | |
|||
| 25. Round | 22/04/2019 | Floriana FC | - | St. Andrews FC | 0:1 |
Jamaica