| 1. Round | 16/08/2018 | Lincoln Red Imps | - | Glacis United FC | 4:0 |  |
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| 5. Round | 22/10/2018 | Lincoln Red Imps | - | Gibraltar United FC | 0:1 |  |
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| 6. Round | 27/10/2018 | Lynx FC | - | Lincoln Red Imps | 1:1 | |
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| 7. Round | 02/11/2018 | Lincoln Red Imps | - | Boca Gibraltar | 3:0 | |
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| 9. Round | 25/11/2018 | Lincoln Red Imps | - | Europa FC | 3:2 | |
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| 9. Round | 30/11/2018 | Mons Calpe S.C. | - | Lincoln Red Imps | 2:2 |
Spain