| 1. Round | 15/08/2018 | Lynx FC | - | Gibraltar Phoenix | 0:0 | ||||
| 2. Round | 19/08/2018 | Gibraltar Phoenix | - | Lincoln Red Imps | 0:2 | ||||
| 5. Round | 20/10/2018 | Glacis United FC | - | Gibraltar Phoenix | 1:3 | ||||
| 7. Round | 01/11/2018 | Gibraltar Phoenix | - | Lions Gibraltar | 1:0 | ||||
| 8. Round | 24/11/2018 | St. Joseph's FC | - | Gibraltar Phoenix | 0:0 | ||||
| 12. Round | 18/12/2018 | Lincoln Red Imps | - | Gibraltar Phoenix | 4:0 | ||||
| 13. Round | 07/01/2019 | Mons Calpe S.C. | - | Gibraltar Phoenix | 3:0 |  |
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| 14. Round | 19/01/2019 | Gibraltar Phoenix | - | Glacis United FC | 6:0 | ||||
| 15. Round | 27/01/2019 | Gibraltar Phoenix | - | Boca Gibraltar | 3:1 |  |
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| 16. Round | 01/02/2019 | Lions Gibraltar | - | Gibraltar Phoenix | 1:3 | ||||
| 17. Round | 17/02/2019 | Gibraltar Phoenix | - | St. Joseph's FC | 1:2 | ||||
| 18. Round | 22/02/2019 | Gibraltar United FC | - | Gibraltar Phoenix | 1:1 | |
Spain