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1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2019
1/16-finals
| 1 | Gibraltar Phoenix | Bye | |
| 2 | Bye | Lynx | |
| 3 | Glacis United | Bye | |
| 4 | Bye | Lions Gibraltar | |
| 5 | Magpies | Leo FC | 10 : 0 |
| 6 | Bye | Boca Gibraltar | |
| 7 | Lincoln Red Imps | Bye | |
| 8 | Bye | Europa FC | |
| 9 | Gibraltar United | Bye | |
| 10 | Bye | Manchester 62 | |
| 11 | Europa Point | Bye | |
| 12 | Bye | Olympique | |
| 13 | St Josephs | Bye | |
| 14 | Bye | Hound Dogs | |
| 15 | College 1975 FC | Bye | |
| 16 | Bye | Mons Calpe |
1/8-finals
| 1 | Gibraltar Phoenix | Lynx | 3 : 1 |
| 2 | Glacis United | Lions Gibraltar | 1 : 2 |
| 3 | Magpies | Boca Gibraltar | 5 : 2 |
| 4 | Lincoln Red Imps | Europa FC | 1 : 2 |
| 5 | Gibraltar United | Manchester 62 | 12 : 0 |
| 6 | Europa Point | Olympique | 0 : 2 |
| 7 | St Josephs | Hound Dogs | 12 : 0 |
| 8 | College 1975 FC | Mons Calpe | 0 : 14 |
Quarter-finals
| 1 | Gibraltar Phoenix | Lions Gibraltar | 4 : 0 |
| 2 | Magpies | Europa FC | 1 : 9 |
| 3 | Gibraltar United | Olympique | 4 : 2 |
| 4 | St Josephs | Mons Calpe | 1 : 4 |
Semi-finals
| 1 | Gibraltar Phoenix | Europa FC | 1 : 4 |
| 2 | Gibraltar United | Mons Calpe | 1 : 0 |
Final
| 1 | Europa FC | Gibraltar United | 3 : 0 |
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