| 12. Round | 15/12/2018 | Europa FC | - | Glacis United FC | 1:0 | ||||
| 13. Round | 14/01/2019 | Glacis United FC | - | Boca Gibraltar | 6:1 |  |
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| 14. Round | 19/01/2019 | Gibraltar Phoenix | - | Glacis United FC | 6:0 | ||||
| 15. Round | 24/01/2019 | Glacis United FC | - | Lions Gibraltar | 3:1 | ||||
| 16. Round | 02/02/2019 | St. Joseph's FC | - | Glacis United FC | 8:0 | ||||
| 17. Round | 15/02/2019 | Glacis United FC | - | Gibraltar United FC | 0:2 | ||||
| 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 | |
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| 21. Round | 28/03/2019 | Mons Calpe S.C. | - | Glacis United FC | 4:1 | ||||
| 22. Round | 07/04/2019 | Boca Gibraltar | - | Glacis United FC | 2:3 |  |
France