| 1. Round | 14/08/2019 | Lions Gibraltar | - | Europa Point FC | 0:0 | ||||
| 1. Round | 23/08/2019 | FCB Magpies | - | Lions Gibraltar | 2:0 |  |
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| 2. Round | 12/09/2019 | Lions Gibraltar | - | Lynx FC | 0:0 | ||||
| 2. Round | 22/09/2019 | Mons Calpe S.C. | - | Lions Gibraltar | 1:1 | ||||
| 2. Round | 29/09/2019 | Lions Gibraltar | - | Lincoln Red Imps | 1:7 | ||||
| 3. Round | 26/10/2019 | Lions Gibraltar | - | St. Joseph's FC | 0:4 | ||||
| 4. Round | 28/11/2019 | College 1975 FC | - | Lions Gibraltar | 1:6 | ||||
| 5. Round | 04/12/2019 | Lions Gibraltar | - | Europa FC | 2:5 | ||||
| 5. Round | 10/12/2019 | Glacis United FC | - | Lions Gibraltar | 1:3 | ||||
| 5. Round | 17/12/2019 | Lions Gibraltar | - | Boca Gibraltar | 6:4 | |
Spain