| 2. Round | 17/08/2018 | St. Joseph's FC | - | Gibraltar United FC | 2:2 | ||||
| 7. Round | 28/10/2018 | Gibraltar United FC | - | Europa FC | 1:3 | ||||
| 8. Round | 23/11/2018 | Gibraltar United FC | - | Glacis United FC | 2:1 | ||||
| 11. Round | 08/12/2018 | Lions Gibraltar | - | Gibraltar United FC | 1:0 | ||||
| 12. Round | 17/12/2018 | Gibraltar United FC | - | St. Joseph's FC | 0:1 | ||||
| 13. Round | 04/01/2019 | Lynx FC | - | Gibraltar United FC | 2:2 | ||||
| 14. Round | 17/01/2019 | Gibraltar United FC | - | Lincoln Red Imps | 1:5 | ||||
| 16. Round | 31/01/2019 | Gibraltar United FC | - | Mons Calpe S.C. | 2:1 | ||||
| 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 |
Gibraltar