| 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 | ||||
| 11. Round | 12/12/2018 | Lions Gibraltar | - | Lincoln Red Imps | 0:2 | ||||
| 12. Round | 18/12/2018 | Lincoln Red Imps | - | Gibraltar Phoenix | 4:0 | ||||
| 13. Round | 03/01/2019 | Lincoln Red Imps | - | St. Joseph's FC | 1:3 | ||||
| 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 | ||||
| 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 |  |
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| 21. Round | 30/03/2019 | Lincoln Red Imps | - | Lions Gibraltar | 5:1 | |
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| 22. Round | 06/04/2019 | St. Joseph's FC | - | Lincoln Red Imps | 1:3 | |
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| 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 | |
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| 26. Round | 11/05/2019 | Lincoln Red Imps | - | Europa FC | 2:0 | |
Spain