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| 26.05.2019 | ||||
| 19:00 | Cup Final | Gibraltar United | 0-3 | Europa FC |
| 10.04.2019 | ||||
| 19:30 | Cup Semifinal | Gibraltar United | 1-0 | Mons Calpe SC |
| 09.04.2019 | ||||
| 19:30 | Cup Semifinal | Gibraltar Phoenix | 1-4 | Europa FC |
| 13.03.2019 | ||||
| 20:30 | Cup Quarterfinal | FCB Magpies | 1-9 | Europa FC |
| 18:15 | Cup Quarterfinal | Gibraltar Phoenix | 4-0 | Lions Gibraltar |
| 12.03.2019 | ||||
| 20:30 | Cup Quarterfinal | St Joseph's (GIB) | 1-4 | Mons Calpe SC |
| 18:15 | Cup Quarterfinal | Gibraltar United | 4-2 | FC Olympique 13 |
| 10.02.2019 | ||||
| 16:00 | Cup Round 2 | Boca Juniors Gibraltar | 2-5 | FCB Magpies |
| 09.02.2019 | ||||
| 20:30 | Cup Round 2 | Europa Point | 0-2 | FC Olympique 13 |
| 18:15 | Cup Round 2 | Glacis United | 1-1/p.3-4 | Lions Gibraltar |
| 16:00 | Cup Round 2 | Lynx FC | 1-3 | Gibraltar Phoenix |
| 08.02.2019 | ||||
| 20:30 | Cup Round 2 | Manchester 62 FC | 0-12 | Gibraltar United |
| 07.02.2019 | ||||
| 20:30 | Cup Round 2 | Lincoln Red Imps | 1-2 | Europa FC |
| 18:15 | Cup Round 2 | Mons Calpe SC | 14-0 | College 1975 |
| 06.02.2019 | ||||
| 20:30 | Cup Round 2 | St Joseph's (GIB) | 12-0 | FC Hound Dogs |
| 20.01.2019 | ||||
| 18:15 | Cup Round 1 | Leo Parrilla FC | 0-10 | FCB Magpies |