| 1. Round | 13/08/2018 | St. Joseph's FC | - | Boca Gibraltar | 5:0 |  |
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| 2. Round | 17/08/2018 | St. Joseph's FC | - | Gibraltar United FC | 2:2 |  |
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| 3. Round | 23/08/2018 | Lynx FC | - | St. Joseph's FC | 2:3 | ||||
| 4. Round | 01/10/2018 | St. Joseph's FC | - | Lincoln Red Imps | 0:5 | |
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| 8. Round | 24/11/2018 | St. Joseph's FC | - | Gibraltar Phoenix | 0:0 | ||||
| 9. Round | 01/12/2018 | Lions Gibraltar | - | St. Joseph's FC | 0:7 | |
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| 10. Round | 06/12/2018 | Boca Gibraltar | - | St. Joseph's FC | 1:1 | ||||
| 13. Round | 03/01/2019 | Lincoln Red Imps | - | St. Joseph's FC | 1:3 | |
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| 14. Round | 19/01/2019 | St. Joseph's FC | - | Europa FC | 0:1 | |
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| 15. Round | 25/01/2019 | Mons Calpe S.C. | - | St. Joseph's FC | 2:1 | ||||
| 16. Round | 02/02/2019 | St. Joseph's FC | - | Glacis United FC | 8:0 | |
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| 17. Round | 17/02/2019 | Gibraltar Phoenix | - | St. Joseph's FC | 1:2 | ||||
| 18. Round | 23/02/2019 | St. Joseph's FC | - | Lions Gibraltar | 3:1 | ||||
| 20. Round | 09/03/2019 | St. Joseph's FC | - | Gibraltar United FC | 2:1 | ||||
| 25. Round | 03/05/2019 | Glacis United FC | - | St. Joseph's FC | 0:1 | ||||
| 26. Round | 10/05/2019 | St. Joseph's FC | - | Gibraltar Phoenix | 3:0 | |
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| 27. Round | 17/05/2019 | Lions Gibraltar | - | St. Joseph's FC | 0:1 |
Gibraltar