| 5. Round | 21/10/2018 | Mons Calpe S.C. | - | Lions Gibraltar | 3:0 | ||||
| 6. Round | 26/10/2018 | Lions Gibraltar | - | Glacis United FC | 0:1 |  |
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| 7. Round | 01/11/2018 | Gibraltar Phoenix | - | Lions Gibraltar | 1:0 | |
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| 8. Round | 22/11/2018 | Boca Gibraltar | - | Lions Gibraltar | 1:0 | ||||
| 11. Round | 08/12/2018 | Lions Gibraltar | - | Gibraltar United FC | 1:0 | ||||
| 11. Round | 12/12/2018 | Lions Gibraltar | - | Lincoln Red Imps | 0:2 | ||||
| 17. Round | 18/02/2019 | Lions Gibraltar | - | Boca Gibraltar | 2:1 | ||||
| 18. Round | 23/02/2019 | St. Joseph's FC | - | Lions Gibraltar | 3:1 | ||||
| 19. Round | 03/03/2019 | Gibraltar United FC | - | Lions Gibraltar | 4:1 | ||||
| 20. Round | 10/03/2019 | Lions Gibraltar | - | Lynx FC | 0:3 | ||||
| 21. Round | 30/03/2019 | Lincoln Red Imps | - | Lions Gibraltar | 5:1 | ||||
| 22. Round | 04/04/2019 | Lions Gibraltar | - | Europa FC | 0:8 | ||||
| 23. Round | 15/04/2019 | Mons Calpe S.C. | - | Lions Gibraltar | 6:0 | ||||
| 24. Round | 27/04/2019 | Lions Gibraltar | - | Glacis United FC | 1:2 | ||||
| 25. Round | 06/05/2019 | Gibraltar Phoenix | - | Lions Gibraltar | 1:0 | ||||
| 26. Round | 11/05/2019 | Boca Gibraltar | - | Lions Gibraltar | 0:7 |
Gibraltar