| British Crown Colony until 1981, British Dependant Territory 1981-2002, British Overseas Territory 2002 => | |||||||||
| GIBRALTAR 1900-01 | |||||||||
| (Merchants Cup) | |||||||||
| Winners | Princes of Wales FC | ||||||||
| GIBRALTAR 1901-02 | |||||||||
| (Merchants Cup) | |||||||||
| Winners | Exiles FC | ||||||||
| GIBRALTAR 1902-03 | |||||||||
| (Merchants Cup) | |||||||||
| Winners | Princes of Wales FC | ||||||||
| GIBRALTAR 1903-04 | |||||||||
| (Merchants Cup) | |||||||||
| Winners | Princes of Wales FC | ||||||||
| GIBRALTAR 1904-05 | |||||||||
| (Merchants Cup) | |||||||||
| Winners | Athletic FC | ||||||||
| GIBRALTAR 1905-06 | |||||||||
| (Merchants Cup) | |||||||||
| GIBRALTAR 1906-07 | |||||||||
| === | Princes of Wales FC | ||||||||
| GIBRALTAR 1907-08 | |||||||||
| Winners | Britannia FC | ||||||||
| GIBRALTAR 1908-09 | |||||||||
| 1 | Princes of Wales FC | ||||||||
| Dockyard United FC | |||||||||
| Ex Pupils FC | |||||||||
| Coronation FC | |||||||||
| Exiles FC | |||||||||
| Britannia FC | |||||||||
| Alexandra FC | |||||||||
| Royal Naval Depot FC | |||||||||
| GIBRALTAR 1909-10 | |||||||||
| Winners | South United FC | ||||||||