| 17. Round | 15/02/2019 | Glacis United FC | - | Gibraltar United FC | 0:2 | ||||
| 19. Round | 03/03/2019 | Gibraltar United FC | - | Lions Gibraltar | 4:1 | ||||
| 21. Round | 30/03/2019 | Gibraltar United FC | - | Boca Gibraltar | 7:0 | ||||
| 24. Round | 28/04/2019 | Gibraltar United FC | - | Europa FC | 1:1 | ||||
| 25. Round | 04/05/2019 | Mons Calpe S.C. | - | Gibraltar United FC | 5:2 | ||||
| 27. Round | 19/05/2019 | Gibraltar Phoenix | - | Gibraltar United FC | 2:0 |
Azerbaijan