| 15. Round | 27/01/2019 | Gibraltar Phoenix | - | Boca Gibraltar | 3:1 | ||||
| 18. Round | 23/02/2019 | Boca Gibraltar | - | Europa FC | 0:9 | ||||
| 19. Round | 28/02/2019 | St. Joseph's FC | - | Boca Gibraltar | 10:1 |  |
|||
| 21. Round | 30/03/2019 | Gibraltar United FC | - | Boca Gibraltar | 7:0 | ||||
| 24. Round | 25/04/2019 | Boca Gibraltar | - | Gibraltar Phoenix | 0:8 | ||||
| 25. Round | 05/05/2019 | Lincoln Red Imps | - | Boca Gibraltar | 10:0 | ||||
| 26. Round | 11/05/2019 | Boca Gibraltar | - | Lions Gibraltar | 0:7 | ||||
| 27. Round | 18/05/2019 | Europa FC | - | Boca Gibraltar | 13:1 |
Gibraltar