| 3. Round | 25/08/2018 | Europa FC | - | Gibraltar Phoenix | 2:0 |  |
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| 4. Round | 03/10/2018 | Gibraltar Phoenix | - | Mons Calpe S.C. | 1:0 | ||||
| 5. Round | 20/10/2018 | Glacis United FC | - | Gibraltar Phoenix | 1:3 | ||||
| 6. Round | 24/10/2018 | Gibraltar Phoenix | - | Europa FC | 0:1 | ||||
| 6. Round | 27/10/2018 | Boca Gibraltar | - | Gibraltar Phoenix | 2:5 | ||||
| 7. Round | 01/11/2018 | Gibraltar Phoenix | - | Lions Gibraltar | 1:0 | ||||
| 8. Round | 24/11/2018 | St. Joseph's FC | - | Gibraltar Phoenix | 0:0 | ||||
| 10. Round | 02/12/2018 | Gibraltar Phoenix | - | Gibraltar United FC | 2:1 | |
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| 10. Round | 07/12/2018 | Gibraltar Phoenix | - | Lynx FC | 2:0 | ||||
| 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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| 23. Round | 14/04/2019 | Glacis United FC | - | Gibraltar Phoenix | 1:1 | ||||
| 24. Round | 25/04/2019 | Boca Gibraltar | - | Gibraltar Phoenix | 0:8 | ||||
| 25. Round | 06/05/2019 | Gibraltar Phoenix | - | Lions Gibraltar | 1:0 | |
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| 26. Round | 10/05/2019 | St. Joseph's FC | - | Gibraltar Phoenix | 3:0 | ||||
| 27. Round | 19/05/2019 | Gibraltar Phoenix | - | Gibraltar United FC | 2:0 |
Spain