| 1. Round | 27/09/2015 | Britannia FC | - | Gibraltar United FC | 1:1 |  |
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| 2. Round | 03/10/2015 | Gibraltar United FC | - | Europa FC | 0:2 | ||||
| 3. Round | 16/10/2015 | Lincoln Red Imps | - | Gibraltar United FC | 7:0 | ||||
| 6. Round | 07/11/2015 | Lynx FC | - | Gibraltar United FC | 3:0 | ||||
| 7. Round | 13/11/2015 | Gibraltar United FC | - | St. Joseph's FC | 0:2 | ||||
| 9. Round | 28/11/2015 | Gibraltar United FC | - | Manchester 62 FC | 1:0 |
Ireland