2. Round | 18/08/2018 | Boca Gibraltar | - | Mons Calpe S.C. | 0:3 | ||||
3. Round | 25/08/2018 | Mons Calpe S.C. | - | Glacis United FC | 0:1 | ||||
8. Round | 24/11/2018 | Lynx FC | - | Mons Calpe S.C. | 0:3 | ||||
15. Round | 25/01/2019 | Mons Calpe S.C. | - | St. Joseph's FC | 2:1 | ||||
16. Round | 31/01/2019 | Gibraltar United FC | - | Mons Calpe S.C. | 2:1 | ||||
23. Round | 15/04/2019 | Mons Calpe S.C. | - | Lions Gibraltar | 6:0 | ||||
25. Round | 04/05/2019 | Mons Calpe S.C. | - | Gibraltar United FC | 5:2 | ||||
27. Round | 18/05/2019 | Mons Calpe S.C. | - | Lincoln Red Imps | 2:0 |