| 2. Round | 12/09/2019 | Lions Gibraltar | - | Lynx FC | 0:0 |  |
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| 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 | |
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| 3. Round | 31/10/2019 | Manchester 62 FC | - | Lions Gibraltar | 0:3 |
Argentina