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GMT 02:00
| 29.09.2023 | |||
| 21:00 | Glacis United | 3-1 | Europa Point |
| 28.09.2023 | |||
| 21:00 | St Joseph's (GIB) | 1-0 | Lincoln Red Imps |
| 27.09.2023 | |||
| 21:00 | College 1975 | 2-1 | Lions Gibraltar |
| 24.09.2023 | |||
| 19:30 | Mons Calpe SC | 2-4 | FCB Magpies |
| 16:30 | Lincoln Red Imps | 3-2 | Lynx FC |
| 23.09.2023 | |||
| 19:30 | Manchester 62 FC | 5-0 | Glacis United |
| 16:30 | Lions Gibraltar | 1-5 | St Joseph's (GIB) |
| 22.09.2023 | |||
| 21:00 | Europa FC | 0-3 | College 1975 |
| 17.09.2023 | |||
| 19:30 | Glacis United | 2-1 | Mons Calpe SC |
| 16:30 | Lynx FC | 4-1 | Lions Gibraltar |
| 16.09.2023 | |||
| 19:30 | St Joseph's (GIB) | 3-0 | Europa FC |
| 16:30 | Europa Point | 1-5 | Manchester 62 FC |
| 30.09.2023 | ||||
| 16:30 | Lynx FC | - | Mons Calpe SC | |
| 19:30 | FCB Magpies | - | Manchester 62 FC | |
| 03.10.2023 | ||||
| 21:00 | College 1975 | - | St Joseph's (GIB) | |
| 04.10.2023 | ||||
| 21:00 | Lincoln Red Imps | - | Glacis United | |
| 05.10.2023 | ||||
| 21:00 | Lions Gibraltar | - | FCB Magpies | |
| 06.10.2023 | ||||
| 21:00 | Europa FC | - | Lynx FC | |
| 07.10.2023 | ||||
| 19:00 | Mons Calpe SC | - | Europa Point | |
| 20.10.2023 | ||||
| 21:00 | Manchester 62 FC | - | Mons Calpe SC | |
| 21.10.2023 | ||||
| 16:30 | FCB Magpies | - | Europa FC | |
| 19:30 | Europa Point | - | Lincoln Red Imps | |
| 22.10.2023 | ||||
| 16:30 | Glacis United | - | Lions Gibraltar | |
| 19:30 | Lynx FC | - | College 1975 | |
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