| 1. Round | 22/09/2016 | Manchester 62 FC | - | Gibraltar United FC | 2:2 |  |
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| 2. Round | 30/09/2016 | Gibraltar United FC | - | Lincoln Red Imps | 0:2 | |
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| 3. Round | 15/10/2016 | Mons Calpe S.C. | - | Gibraltar United FC | 3:1 | ||||
| 4. Round | 22/10/2016 | Gibraltar United FC | - | St. Joseph's FC | 0:1 |  |
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| 6. Round | 04/11/2016 | Lions Gibraltar | - | Gibraltar United FC | 0:0 | ||||
| 19. Round | 04/03/2017 | Manchester 62 FC | - | Gibraltar United FC | 3:0 | ||||
| 20. Round | 17/03/2017 | Gibraltar United FC | - | Lincoln Red Imps | 0:1 | ||||
| 21. Round | 01/04/2017 | Mons Calpe S.C. | - | Gibraltar United FC | 2:1 | ||||
| 22. Round | 09/04/2017 | Gibraltar United FC | - | St. Joseph's FC | 0:0 | ||||
| 23. Round | 22/04/2017 | Lynx FC | - | Gibraltar United FC | 1:1 | |
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| 24. Round | 29/04/2017 | Lions Gibraltar | - | Gibraltar United FC | 0:0 | ||||
| 25. Round | 06/05/2017 | Gibraltar United FC | - | Glacis United FC | 2:1 | ||||
| 26. Round | 12/05/2017 | Europa FC | - | Gibraltar United FC | 7:0 | ||||
| 27. Round | 22/05/2017 | Gibraltar United FC | - | Europa Point FC | 2:2 |
Gibraltar