| 1. Jornada | 19.08.2019 | St. Joseph's FC | - | College 1975 FC | 7:0 |  |
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| 1. Jornada | 24.08.2019 | St. Joseph's FC | - | Manchester 62 FC | 3:0 | ||||
| 2. Jornada | 14.09.2019 | St. Joseph's FC | - | Boca Gibraltar | 2:0 | |
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| 2. Jornada | 25.09.2019 | Europa FC | - | St. Joseph's FC | 2:2 |  |
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| 3. Jornada | 20.10.2019 | St. Joseph's FC | - | Glacis United FC | 8:1 | ||||
| 3. Jornada | 26.10.2019 | Lions Gibraltar | - | St. Joseph's FC | 0:4 | |
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| 4. Jornada | 24.11.2019 | Mons Calpe S.C. | - | St. Joseph's FC | 0:6 | ||||
| 4. Jornada | 30.11.2019 | St. Joseph's FC | - | Europa Point FC | 5:0 | ||||
| 5. Jornada | 07.12.2019 | FCB Magpies | - | St. Joseph's FC | 0:3 | ||||
| 5. Jornada | 13.12.2019 | St. Joseph's FC | - | Lincoln Red Imps | 2:1 | |
España