| 1. Round | 14/08/2018 | Gibraltar United FC | - | Lions Gibraltar | 4:0 | ||||
| 4. Round | 04/10/2018 | Gibraltar United FC | - | Lynx FC | 4:1 | ||||
| 5. Round | 22/10/2018 | Lincoln Red Imps | - | Gibraltar United FC | 0:1 | ||||
| 8. Round | 23/11/2018 | Gibraltar United FC | - | Glacis United FC | 2:1 | ||||
| 9. Round | 27/11/2018 | Boca Gibraltar | - | Gibraltar United FC | 0:4 | ||||
| 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 |
Gibraltar