| 1. Round | 13/08/2018 | St. Joseph's FC | - | Boca Gibraltar | 5:0 | ||||
| 2. Round | 18/08/2018 | Boca Gibraltar | - | Mons Calpe S.C. | 0:3 |  |
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| 4. Round | 02/10/2018 | Boca Gibraltar | - | Glacis United FC | 0:2 | |
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| 5. Round | 19/10/2018 | Lynx FC | - | Boca Gibraltar | 0:1 | |
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| 10. Round | 06/12/2018 | Boca Gibraltar | - | St. Joseph's FC | 1:1 | |
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| 15. Round | 27/01/2019 | Gibraltar Phoenix | - | Boca Gibraltar | 3:1 |  |
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| 27. Round | 18/05/2019 | Europa FC | - | Boca Gibraltar | 13:1 |
Gibraltar