| 1. Round | 22/09/2016 | Manchester 62 FC | - | Gibraltar United FC | 2:2 | ||||
| 8. Round | 27/11/2016 | Europa FC | - | Gibraltar United FC | 3:0 | ||||
| 10. Round | 09/12/2016 | Gibraltar United FC | - | Manchester 62 FC | 3:1 | ||||
| 11. Round | 17/12/2016 | Lincoln Red Imps | - | Gibraltar United FC | 2:0 | ||||
| 12. Round | 08/01/2017 | Gibraltar United FC | - | Mons Calpe S.C. | 2:2 | ||||
| 13. Round | 15/01/2017 | St. Joseph's FC | - | Gibraltar United FC | 4:1 | ||||
| 14. Round | 21/01/2017 | Gibraltar United FC | - | Lynx FC | 0:1 | ||||
| 17. Round | 20/02/2017 | Gibraltar United FC | - | Europa FC | 0:1 | ||||
| 18. Round | 25/02/2017 | Europa Point FC | - | Gibraltar United FC | 1:0 |  |
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| 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 | |
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| 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 |  |
England