1. Round | 12/08/2019 | Lynx FC | - | Mons Calpe S.C. | 5:1 | ||||
2. Round | 13/09/2019 | Glacis United FC | - | Mons Calpe S.C. | 0:5 | ||||
2. Round | 22/09/2019 | Mons Calpe S.C. | - | Lions Gibraltar | 1:1 | ||||
2. Round | 29/09/2019 | Boca Gibraltar | - | Mons Calpe S.C. | 1:1 | ||||
3. Round | 05/10/2019 | Mons Calpe S.C. | - | Europa Point FC | 0:2 | ||||
3. Round | 19/10/2019 | FCB Magpies | - | Mons Calpe S.C. | 1:3 | ||||
4. Round | 24/11/2019 | Mons Calpe S.C. | - | St. Joseph's FC | 0:6 |