| 4. Ronde | 01.10.2018 | St. Joseph's FC | - | Lincoln Red Imps | 0:5 | ||||
| 5. Ronde | 20.10.2018 | Europa FC | - | St. Joseph's FC | 2:3 | ||||
| 11. Ronde | 11.12.2018 | St. Joseph's FC | - | Lynx FC | 7:1 |  |
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| 16. Ronde | 02.02.2019 | St. Joseph's FC | - | Glacis United FC | 8:0 | ||||
| 17. Ronde | 17.02.2019 | Gibraltar Phoenix | - | St. Joseph's FC | 1:2 | ||||
| 19. Ronde | 28.02.2019 | St. Joseph's FC | - | Boca Gibraltar | 10:1 | ||||
| 20. Ronde | 09.03.2019 | St. Joseph's FC | - | Gibraltar United FC | 2:1 | ||||
| 21. Ronde | 31.03.2019 | Lynx FC | - | St. Joseph's FC | 0:1 |  |
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| 23. Ronde | 13.04.2019 | Europa FC | - | St. Joseph's FC | 2:0 | |
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| 26. Ronde | 10.05.2019 | St. Joseph's FC | - | Gibraltar Phoenix | 3:0 | ||||
| 27. Ronde | 17.05.2019 | Lions Gibraltar | - | St. Joseph's FC | 0:1 |
Engeland
Gibraltar