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