| 1. Ronde | 16.08.2018 | Lincoln Red Imps | - | Glacis United FC | 4:0 |  |
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| 2. Ronde | 19.08.2018 | Gibraltar Phoenix | - | Lincoln Red Imps | 0:2 | |
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| 3. Ronde | 24.08.2018 | Lincoln Red Imps | - | Lions Gibraltar | 3:0 | |
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| 5. Ronde | 22.10.2018 | Lincoln Red Imps | - | Gibraltar United FC | 0:1 | ||||
| 6. Ronde | 27.10.2018 | Lynx FC | - | Lincoln Red Imps | 1:1 | ||||
| 7. Ronde | 02.11.2018 | Lincoln Red Imps | - | Boca Gibraltar | 3:0 | ||||
| 9. Ronde | 25.11.2018 | Lincoln Red Imps | - | Europa FC | 3:2 | |
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| 11. Ronde | 12.12.2018 | Lions Gibraltar | - | Lincoln Red Imps | 0:2 | |
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| 12. Ronde | 18.12.2018 | Lincoln Red Imps | - | Gibraltar Phoenix | 4:0 | ||||
| 13. Ronde | 03.01.2019 | Lincoln Red Imps | - | St. Joseph's FC | 1:3 | |
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| 14. Ronde | 17.01.2019 | Gibraltar United FC | - | Lincoln Red Imps | 1:5 | |
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| 15. Ronde | 26.01.2019 | Lincoln Red Imps | - | Lynx FC | 1:0 | ||||
| 17. Ronde | 16.02.2019 | Europa FC | - | Lincoln Red Imps | 1:1 | ||||
| 18. Ronde | 24.02.2019 | Lincoln Red Imps | - | Mons Calpe S.C. | 3:1 | |
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| 19. Ronde | 02.03.2019 | Lincoln Red Imps | - | Glacis United FC | 2:1 | |
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| 20. Ronde | 08.03.2019 | Gibraltar Phoenix | - | Lincoln Red Imps | 0:3 | |
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| 26. Ronde | 11.05.2019 | Lincoln Red Imps | - | Europa FC | 2:0 | |
Gibraltar