| 1. Jornada | 16.08.2019 | Europa FC | - | Lincoln Red Imps | 4:1 | ||||
| 2. Jornada | 19.09.2019 | Lincoln Red Imps | - | College 1975 FC | 9:1 |  |
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| 2. Jornada | 29.09.2019 | Lions Gibraltar | - | Lincoln Red Imps | 1:7 | |
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| 3. Jornada | 21.10.2019 | Lincoln Red Imps | - | Lynx FC | 4:0 | ||||
| 3. Jornada | 27.10.2019 | Mons Calpe S.C. | - | Lincoln Red Imps | 0:2 |  |
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| 4. Jornada | 03.11.2019 | Lincoln Red Imps | - | Europa Point FC | 3:0 | ||||
| 4. Jornada | 23.11.2019 | FCB Magpies | - | Lincoln Red Imps | 0:3 | ||||
| 5. Jornada | 13.12.2019 | St. Joseph's FC | - | Lincoln Red Imps | 2:1 | ||||
| 5. Jornada | 19.12.2019 | Lincoln Red Imps | - | Manchester 62 FC | 2:0 |
Gibraltar