| 4. Ronde | 01.10.2018 | St. Joseph's FC | - | Lincoln Red Imps | 0:5 | ||||
| 6. Ronde | 25.10.2018 | St. Joseph's FC | - | Mons Calpe S.C. | 1:2 | ||||
| 8. Ronde | 04.11.2018 | Glacis United FC | - | St. Joseph's FC | 0:2 | ||||
| 9. Ronde | 01.12.2018 | Lions Gibraltar | - | St. Joseph's FC | 0:7 | ||||
| 11. Ronde | 11.12.2018 | St. Joseph's FC | - | Lynx FC | 7:1 | ||||
| 12. Ronde | 17.12.2018 | Gibraltar United FC | - | St. Joseph's FC | 0:1 | ||||
| 18. Ronde | 23.02.2019 | St. Joseph's FC | - | Lions Gibraltar | 3:1 | ||||
| 19. Ronde | 28.02.2019 | St. Joseph's FC | - | Boca Gibraltar | 10:1 |  |
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| 21. Ronde | 31.03.2019 | Lynx FC | - | St. Joseph's FC | 0:1 | ||||
| 22. Ronde | 06.04.2019 | St. Joseph's FC | - | Lincoln Red Imps | 1:3 | ||||
| 23. Ronde | 13.04.2019 | Europa FC | - | St. Joseph's FC | 2:0 | ||||
| 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 | ||||
| 27. Ronde | 17.05.2019 | Lions Gibraltar | - | St. Joseph's FC | 0:1 |
Duitsland