| 1. Round | 14/08/2018 | Gibraltar United FC | - | Lions Gibraltar | 4:0 |  |
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| 2. Round | 17/08/2018 | St. Joseph's FC | - | Gibraltar United FC | 2:2 |  |
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| 3. Round | 22/08/2018 | Gibraltar United FC | - | Boca Gibraltar | 2:1 | |
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| 4. Round | 04/10/2018 | Gibraltar United FC | - | Lynx FC | 4:1 |
| James Louis Bosio | |
| Born: | 24.09.1991 |
| Place of birth: |
Dublin, 
Ireland |
| Nationality: |
Gibraltar
Ireland |
| Height: | 179 cm |
| Weight: | 75 kg |
| Position(s): | Defensive Midfielder Left Back |
| Foot: | left |
