| 17. Round | 15/02/2019 | Glacis United FC | - | Gibraltar United FC | 0:2 | ||||
| 18. Round | 21/02/2019 | Lynx FC | - | Glacis United FC | 2:1 | ||||
| 19. Round | 02/03/2019 | Lincoln Red Imps | - | Glacis United FC | 2:1 | ||||
| 20. Round | 07/03/2019 | Glacis United FC | - | Europa FC | 1:6 | ||||
| 22. Round | 07/04/2019 | Boca Gibraltar | - | Glacis United FC | 2:3 | ||||
| 23. Round | 14/04/2019 | Glacis United FC | - | Gibraltar Phoenix | 1:1 | ||||
| 24. Round | 27/04/2019 | Lions Gibraltar | - | Glacis United FC | 1:2 | ||||
| 25. Round | 03/05/2019 | Glacis United FC | - | St. Joseph's FC | 0:1 | ||||
| 26. Round | 13/05/2019 | Gibraltar United FC | - | Glacis United FC | 2:0 | ||||
| 27. Round | 20/05/2019 | Glacis United FC | - | Lynx FC | 0:2 |
Canada