| 14. Round | 17/01/2019 | Gibraltar United FC | - | Lincoln Red Imps | 1:5 |  |
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| 15. Round | 26/01/2019 | Europa FC | - | Gibraltar United FC | 1:0 | |
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| 16. Round | 31/01/2019 | Gibraltar United FC | - | Mons Calpe S.C. | 2:1 |  |
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| 17. Round | 15/02/2019 | Glacis United FC | - | Gibraltar United FC | 0:2 | ||||
| 18. Round | 22/02/2019 | Gibraltar United FC | - | Gibraltar Phoenix | 1:1 | ||||
| 19. Round | 03/03/2019 | Gibraltar United FC | - | Lions Gibraltar | 4:1 | |
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| 20. Round | 09/03/2019 | St. Joseph's FC | - | Gibraltar United FC | 2:1 | ||||
| 21. Round | 30/03/2019 | Gibraltar United FC | - | Boca Gibraltar | 7:0 | |
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| 22. Round | 06/04/2019 | Gibraltar United FC | - | Lynx FC | 1:1 | |
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| 23. Round | 16/04/2019 | Lincoln Red Imps | - | Gibraltar United FC | 2:0 | ||||
| 24. Round | 28/04/2019 | Gibraltar United FC | - | Europa FC | 1:1 | ||||
| 26. Round | 13/05/2019 | Gibraltar United FC | - | Glacis United FC | 2:0 | |
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| 27. Round | 19/05/2019 | Gibraltar Phoenix | - | Gibraltar United FC | 2:0 |
Spain