| 15. Round | 25/01/2019 | Mons Calpe S.C. | - | St. Joseph's FC | 2:1 | ||||
| 16. Round | 31/01/2019 | Gibraltar United FC | - | Mons Calpe S.C. | 2:1 | ||||
| 17. Round | 16/02/2019 | Mons Calpe S.C. | - | Lynx FC | 1:1 | ||||
| 21. Round | 28/03/2019 | Mons Calpe S.C. | - | Glacis United FC | 4:1 |  |
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| 22. Round | 05/04/2019 | Gibraltar Phoenix | - | Mons Calpe S.C. | 0:2 | ||||
| 25. Round | 04/05/2019 | Mons Calpe S.C. | - | Gibraltar United FC | 5:2 | ||||
| 27. Round | 18/05/2019 | Mons Calpe S.C. | - | Lincoln Red Imps | 2:0 |
Argentina
Croatia