| 2. Round | 19/09/2019 | Lincoln Red Imps | - | College 1975 FC | 9:1 | ||||
| 2. Round | 29/09/2019 | Lions Gibraltar | - | Lincoln Red Imps | 1:7 |  |
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| 3. Round | 21/10/2019 | Lincoln Red Imps | - | Lynx FC | 4:0 | ||||
| 3. Round | 27/10/2019 | Mons Calpe S.C. | - | Lincoln Red Imps | 0:2 | ||||
| 4. Round | 03/11/2019 | Lincoln Red Imps | - | Europa Point FC | 3:0 | ||||
| 4. Round | 27/11/2019 | Boca Gibraltar | - | Lincoln Red Imps | 1:8 | |
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| 5. Round | 13/12/2019 | St. Joseph's FC | - | Lincoln Red Imps | 2:1 |  |
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| 5. Round | 19/12/2019 | Lincoln Red Imps | - | Manchester 62 FC | 2:0 |
Gibraltar