| 15. Round | 27/01/2019 | Gibraltar Phoenix | - | Boca Gibraltar | 3:1 | ||||
| 16. Round | 02/02/2019 | Boca Gibraltar | - | Lincoln Red Imps | 0:11 | ||||
| 17. Round | 18/02/2019 | Lions Gibraltar | - | Boca Gibraltar | 2:1 | ||||
| 21. Round | 30/03/2019 | Gibraltar United FC | - | Boca Gibraltar | 7:0 | ||||
| 22. Round | 07/04/2019 | Boca Gibraltar | - | Glacis United FC | 2:3 | ||||
| 24. Round | 25/04/2019 | Boca Gibraltar | - | Gibraltar Phoenix | 0:8 | ||||
| 25. Round | 05/05/2019 | Lincoln Red Imps | - | Boca Gibraltar | 10:0 |  |
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| 26. Round | 11/05/2019 | Boca Gibraltar | - | Lions Gibraltar | 0:7 | ||||
| 27. Round | 18/05/2019 | Europa FC | - | Boca Gibraltar | 13:1 |
Gibraltar