| 1. Round | 13/08/2019 | Manchester 62 FC | - | Boca Gibraltar | 0:0 |  |
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| 1. Round | 24/08/2019 | St. Joseph's FC | - | Manchester 62 FC | 3:0 | |
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| 2. Round | 30/09/2019 | College 1975 FC | - | Manchester 62 FC | 0:3 | |
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| 3. Round | 20/10/2019 | Manchester 62 FC | - | Europa FC | 0:7 | |
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| 3. Round | 26/10/2019 | Glacis United FC | - | Manchester 62 FC | 2:3 | ||||
| 3. Round | 31/10/2019 | Manchester 62 FC | - | Lions Gibraltar | 0:3 | |
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| 5. Round | 07/12/2019 | Europa Point FC | - | Manchester 62 FC | 1:3 | |
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| 5. Round | 19/12/2019 | Lincoln Red Imps | - | Manchester 62 FC | 2:0 |
Gibraltar