| 1. Round | 16/08/2018 | Lincoln Red Imps | - | Glacis United FC | 4:0 |  |
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| 2. Round | 19/08/2018 | Gibraltar Phoenix | - | Lincoln Red Imps | 0:2 | |
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| 3. Round | 24/08/2018 | Lincoln Red Imps | - | Lions Gibraltar | 3:0 | |
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| 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 | |
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| 11. Round | 12/12/2018 | Lions Gibraltar | - | Lincoln Red Imps | 0:2 | |
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| 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 | |
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| 14. Round | 17/01/2019 | Gibraltar United FC | - | Lincoln Red Imps | 1:5 | |
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| 15. Round | 26/01/2019 | Lincoln Red Imps | - | Lynx FC | 1:0 | ||||
| 17. Round | 16/02/2019 | Europa FC | - | Lincoln Red Imps | 1:1 | ||||
| 18. Round | 24/02/2019 | Lincoln Red Imps | - | Mons Calpe S.C. | 3:1 | |
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| 19. Round | 02/03/2019 | Lincoln Red Imps | - | Glacis United FC | 2:1 | |
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| 20. Round | 08/03/2019 | Gibraltar Phoenix | - | Lincoln Red Imps | 0:3 | |
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| 26. Round | 11/05/2019 | Lincoln Red Imps | - | Europa FC | 2:0 | |
Gibraltar