1. Round | 16/08/2019 | Europa FC | - | Lincoln Red Imps | 4:1 | ||||
2. Round | 15/09/2019 | Europa FC | - | Europa Point FC | 1:0 | ||||
2. Round | 20/09/2019 | FCB Magpies | - | Europa FC | 0:6 | ||||
2. Round | 25/09/2019 | Europa FC | - | St. Joseph's FC | 2:2 | ||||
4. Round | 01/11/2019 | College 1975 FC | - | Europa FC | 0:12 | ||||
4. Round | 23/11/2019 | Europa FC | - | Boca Gibraltar | 6:1 | ||||
4. Round | 29/11/2019 | Europa FC | - | Glacis United FC | 6:2 | ||||
5. Round | 04/12/2019 | Lions Gibraltar | - | Europa FC | 2:5 |