| 1. Round | 16/08/2018 | Lincoln Red Imps | - | Glacis United FC | 4:0 | ||||
| 2. Round | 19/08/2018 | Gibraltar Phoenix | - | Lincoln Red Imps | 0:2 | ||||
| 3. Round | 24/08/2018 | Lincoln Red Imps | - | Lions Gibraltar | 3:0 | ||||
| 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 | ||||
| 18. Round | 24/02/2019 | Lincoln Red Imps | - | Mons Calpe S.C. | 3:1 | ||||
| 19. Round | 02/03/2019 | Lincoln Red Imps | - | Glacis United FC | 2:1 | ||||
| 20. Round | 08/03/2019 | Gibraltar Phoenix | - | Lincoln Red Imps | 0:3 | ||||
| 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 |  |
|||
| 26. Round | 11/05/2019 | Lincoln Red Imps | - | Europa FC | 2:0 | |
England