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2024 2023 2022 2021 2020 2019 2017/18 2016/17 2015/16 2014/15
1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2015/16
1/16-finals
| 1 | Lincoln Red Imps | Bye | |
| 2 | Bye | Britannia XI | |
| 3 | Magpies | Cannons | 3 : 1 |
| 4 | Bye | Glacis United | |
| 5 | College 1975 FC | Pegasus | 5 : 2 |
| 6 | Boca Gibraltar | Leo FC | 0 : 2 |
| 7 | Lynx | Bye | |
| 8 | Bye | Manchester 62 | |
| 9 | Europa FC | Bye | |
| 10 | Bye | St Josephs | |
| 11 | Gibraltar Phoenix | Hound Dogs | 4 : 0 |
| 12 | Bye | Angels | |
| 13 | Gibraltar United | Bye | |
| 14 | Olympique | Red Imps | 1 : 3 |
| 15 | Mons Calpe | Europa Point | 2 : 1 |
| 16 | Bye | Lions Gibraltar |
1/8-finals
| 1 | Lincoln Red Imps | Britannia XI | 5 : 1 |
| 2 | Magpies | Glacis United | 0 : 7 |
| 3 | College 1975 FC | Leo FC | 1 : 0 |
| 4 | Lynx | Manchester 62 | 0 : 1 |
| 5 | Europa FC | St Josephs | 1 : 0 |
| 6 | Gibraltar Phoenix | Angels | 0 : 4 |
| 7 | Gibraltar United | Red Imps | 2 : 1 |
| 8 | Mons Calpe | Lions Gibraltar | 1 : 4 |
Quarter-finals
| 1 | Lincoln Red Imps | Glacis United | 4 : 0 |
| 2 | College 1975 FC | Manchester 62 | 0 : 7 |
| 3 | Europa FC | Angels | 4 : 1 |
| 4 | Gibraltar United | Lions Gibraltar | 0 : 1 |
Semi-finals
| 1 | Lincoln Red Imps | Manchester 62 | 6 : 2 |
| 2 | Europa FC | Lions Gibraltar | 1 : 0 |
Final
| 1 | Lincoln Red Imps | Europa FC | 2 : 0 |
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