| 1. Ronde | 13.08.2018 | St. Joseph's FC | - | Boca Gibraltar | 5:0 |  |
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| 2. Ronde | 17.08.2018 | St. Joseph's FC | - | Gibraltar United FC | 2:2 |  |
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| 3. Ronde | 23.08.2018 | Lynx FC | - | St. Joseph's FC | 2:3 | ||||
| 4. Ronde | 01.10.2018 | St. Joseph's FC | - | Lincoln Red Imps | 0:5 | |
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| 8. Ronde | 24.11.2018 | St. Joseph's FC | - | Gibraltar Phoenix | 0:0 | ||||
| 9. Ronde | 01.12.2018 | Lions Gibraltar | - | St. Joseph's FC | 0:7 | |
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| 10. Ronde | 06.12.2018 | Boca Gibraltar | - | St. Joseph's FC | 1:1 | ||||
| 13. Ronde | 03.01.2019 | Lincoln Red Imps | - | St. Joseph's FC | 1:3 | |
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| 14. Ronde | 19.01.2019 | St. Joseph's FC | - | Europa FC | 0:1 | |
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| 15. Ronde | 25.01.2019 | Mons Calpe S.C. | - | St. Joseph's FC | 2:1 | ||||
| 16. Ronde | 02.02.2019 | St. Joseph's FC | - | Glacis United FC | 8:0 | |
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| 17. Ronde | 17.02.2019 | Gibraltar Phoenix | - | St. Joseph's FC | 1:2 | ||||
| 18. Ronde | 23.02.2019 | St. Joseph's FC | - | Lions Gibraltar | 3:1 | ||||
| 20. Ronde | 09.03.2019 | St. Joseph's FC | - | Gibraltar United FC | 2:1 | ||||
| 25. Ronde | 03.05.2019 | Glacis United FC | - | St. Joseph's FC | 0:1 | ||||
| 26. Ronde | 10.05.2019 | St. Joseph's FC | - | Gibraltar Phoenix | 3:0 | |
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| 27. Ronde | 17.05.2019 | Lions Gibraltar | - | St. Joseph's FC | 0:1 |
Gibraltar