| 3. Round | 24/08/2018 | Lincoln Red Imps | - | Lions Gibraltar | 3:0 | ||||
| 4. Round | 01/10/2018 | St. Joseph's FC | - | Lincoln Red Imps | 0:5 | ||||
| 5. Round | 22/10/2018 | Lincoln Red Imps | - | Gibraltar United FC | 0:1 | ||||
| 6. Round | 27/10/2018 | Lynx FC | - | Lincoln Red Imps | 1:1 | ||||
| 7. Round | 02/11/2018 | Lincoln Red Imps | - | Boca Gibraltar | 3:0 | ||||
| 9. Round | 25/11/2018 | Lincoln Red Imps | - | Europa FC | 3:2 | ||||
| 9. Round | 30/11/2018 | Mons Calpe S.C. | - | Lincoln Red Imps | 2:2 | ||||
| 11. Round | 08/12/2018 | Glacis United FC | - | Lincoln Red Imps | 1:2 | ||||
| 14. Round | 17/01/2019 | Gibraltar United FC | - | Lincoln Red Imps | 1:5 | ||||
| 15. Round | 26/01/2019 | Lincoln Red Imps | - | Lynx FC | 1:0 | ||||
| 16. Round | 02/02/2019 | Boca Gibraltar | - | Lincoln Red Imps | 0:11 |  |
|||
| 21. Round | 30/03/2019 | Lincoln Red Imps | - | Lions Gibraltar | 5:1 | ||||
| 22. Round | 06/04/2019 | St. Joseph's FC | - | Lincoln Red Imps | 1:3 | ||||
| 23. Round | 16/04/2019 | Lincoln Red Imps | - | Gibraltar United FC | 2:0 |  |
|||
| 24. Round | 26/04/2019 | Lynx FC | - | Lincoln Red Imps | 1:4 | ||||
| 25. Round | 05/05/2019 | Lincoln Red Imps | - | Boca Gibraltar | 10:0 | ||||
| 26. Round | 11/05/2019 | Lincoln Red Imps | - | Europa FC | 2:0 |
Gibraltar