| 2. Journée | 15.09.2019 | College 1975 FC | - | FCB Magpies | 1:3 |  |
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| 2. Journée | 19.09.2019 | Lincoln Red Imps | - | College 1975 FC | 9:1 | ||||
| 2. Journée | 30.09.2019 | College 1975 FC | - | Manchester 62 FC | 0:3 | ||||
| 3. Journée | 24.10.2019 | College 1975 FC | - | Boca Gibraltar | 0:4 | |
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| 4. Journée | 22.11.2019 | Glacis United FC | - | College 1975 FC | 4:0 | ||||
| 4. Journée | 28.11.2019 | College 1975 FC | - | Lions Gibraltar | 1:6 | |
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| 5. Journée | 06.12.2019 | Lynx FC | - | College 1975 FC | 4:0 | ||||
| 5. Journée | 16.12.2019 | Europa Point FC | - | College 1975 FC | 6:1 |  |
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Gibraltar