| 13. Round | 04/01/2019 | Lynx FC | - | Gibraltar United FC | 2:2 | ||||
| 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 | ||||
| 16. Round | 31/01/2019 | Gibraltar United FC | - | Mons Calpe S.C. | 2:1 | ||||
| 17. Round | 15/02/2019 | Glacis United FC | - | Gibraltar United FC | 0:2 | |
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| 18. Round | 22/02/2019 | Gibraltar United FC | - | Gibraltar Phoenix | 1:1 | ||||
| 22. Round | 06/04/2019 | Gibraltar United FC | - | Lynx FC | 1:1 | ||||
| 23. Round | 16/04/2019 | Lincoln Red Imps | - | Gibraltar United FC | 2:0 |  |
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| 24. Round | 28/04/2019 | Gibraltar United FC | - | Europa FC | 1:1 | |
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| 25. Round | 04/05/2019 | Mons Calpe S.C. | - | Gibraltar United FC | 5:2 | ||||
| 27. Round | 19/05/2019 | Gibraltar Phoenix | - | Gibraltar United FC | 2:0 |
Argentina
Italy