| 16. Round | 01/02/2019 | Lions Gibraltar | - | Gibraltar Phoenix | 1:3 | ||||
| 17. Round | 17/02/2019 | Gibraltar Phoenix | - | St. Joseph's FC | 1:2 | ||||
| 18. Round | 22/02/2019 | Gibraltar United FC | - | Gibraltar Phoenix | 1:1 | ||||
| 19. Round | 02/03/2019 | Lynx FC | - | Gibraltar Phoenix | 1:2 | ||||
| 20. Round | 08/03/2019 | Gibraltar Phoenix | - | Lincoln Red Imps | 0:3 | ||||
| 21. Round | 29/03/2019 | Europa FC | - | Gibraltar Phoenix | 3:0 | ||||
| 22. Round | 05/04/2019 | Gibraltar Phoenix | - | Mons Calpe S.C. | 0:2 | ||||
| 23. Round | 14/04/2019 | Glacis United FC | - | Gibraltar Phoenix | 1:1 | ||||
| 24. Round | 25/04/2019 | Boca Gibraltar | - | Gibraltar Phoenix | 0:8 |  |
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| 25. Round | 06/05/2019 | Gibraltar Phoenix | - | Lions Gibraltar | 1:0 | ||||
| 26. Round | 10/05/2019 | St. Joseph's FC | - | Gibraltar Phoenix | 3:0 | ||||
| 27. Round | 19/05/2019 | Gibraltar Phoenix | - | Gibraltar United FC | 2:0 | |
Gibraltar