| 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 | ||||
| 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 | ||||
| 11. Round | 08/12/2018 | Glacis United FC | - | Lincoln Red Imps | 1:2 | |
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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 | |
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| 13. Round | 03/01/2019 | Lincoln Red Imps | - | St. Joseph's FC | 1:3 | ||||
| 16. Round | 02/02/2019 | Boca Gibraltar | - | Lincoln Red Imps | 0:11 | |
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| 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 | ||||
| 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 | ||||
| 21. Round | 30/03/2019 | Lincoln Red Imps | - | Lions Gibraltar | 5:1 | |
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| 23. Round | 16/04/2019 | Lincoln Red Imps | - | Gibraltar United FC | 2:0 |  |
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| 24. Round | 26/04/2019 | Lynx FC | - | Lincoln Red Imps | 1:4 |
Spain