- 1905/06: Prince of Wales FC
- 1906/07: nicht ausgetragen
- 1907/08: Britannia FC
- 1908/09: Prince of Wales FC
- 1909/10: South United FC
- 1910/11: South United FC
- 1911/12: Britannia FC
- 1912/13: Britannia FC
- 1913/14: Prince of Wales FC
- 1914/15: Royal Sovereign FC
- 1915/16: nicht ausgetragen
- 1916/17: Prince of Wales FC
- 1917/18: Britannia FC
- 1918/19: Prince of Wales FC
- 1919/20: Britannia FC
- 1920/21: Prince of Wales FC
- 1921/22: Prince of Wales FC
- 1922/23: Prince of Wales FC
- 1923/24: Gibraltar FC
- 1924/25: Prince of Wales FC
- 1925/26: Prince of Wales FC
- 1926/27: Prince of Wales FC
- 1927/28: Prince of Wales FC
- 1928/29: Europa FC
- 1929/30: Europa FC
- 1930/31: Prince of Wales FC
- 1931/32: Europa FC
- 1932/33: Europa FC
| - 1933/34: Commander of the Yard FC
- 1934/35: Chief Construction FC
- 1935/36: Chief Constructor FC
- 1936/37: Britannia FC
- 1937/38: Europa FC
- 1938/39: Prince of Wales FC
- 1939/40: Prince of Wales FC
- 1940/41: Britannia FC
- 1942–1945 nicht ausgetragen
- 1946/47: Gibraltar United FC
- 1947/48: Gibraltar United FC
- 1948/49: Gibraltar United FC
- 1949/50: Gibraltar United FC
- 1950/51:Gibraltar United FC
- 1951/52: Europa FC
- 1952/53: Prince of Wales FC
- 1953/54: Gibraltar United FC
- 1954/55: Britannia FC
- 1955/56: Britannia FC
- 1956/57: Britannia FC
- 1957/58: Britannia FC
- 1958/59: Britannia FC
- 1959/60: Gibraltar United FC
- 1960/61: Britannia FC
- 1961/62: Gibraltar United FC
- 1962/63: Britannia FC
- 1963/64: Gibraltar United FC
- 1964/65: Gibraltar United FC
| - 1965/66: Glacis United FC
- 1966/67: Glacis United FC
- 1967/68: Glacis United FC
- 1968/69: Glacis United FC
- 1969/70: Glacis United FC
- 1970/71: Glacis United FC
- 1971/72: Glacis United FC
- 1972/73: Glacis United FC
- 1973/74: Glacis United FC
- 1974/75: Manchester United FC
- 1975/76: Glacis United FC
- 1976/77: Manchester United FC
- 1977/78: nicht ausgetragen
- 1978/79: Manchester United FC
- 1979/80: Manchester United FC
- 1980/81: Glacis United FC
- 1981/82: Glacis United FC
- 1982/83: Glacis United FC
- 1983/84: Manchester United FC
- 1984/85: Glacis United FC
- 1985/86: Lincoln FC
- 1986/87: St Theresas FC
- 1987/88: St Theresas FC
- 1988/89: Glacis United FC
- 1989/90: Lincoln FC
- 1990/91: Lincoln FC
- 1991/92: Lincoln FC
- 1992/93: Lincoln FC
- 1993/94: Lincoln FC
| - 1994/95: Manchester United FC
- 1995/96: St Joseph’s FC
- 1996/97: Glacis United FC
- 1997/98: St Theresas FC
- 1998/99: Manchester United FC
- 1999/00: Glacis United FC
- 2000/01: Lincoln FC
- 2001/02: Gibraltar United FC
- 2002/03: Newcastle United FC1
- 2003/04: Newcastle United FC
- 2004/05: Newcastle United FC
- 2005/06: Newcastle United FC
- 2006/07: Newcastle United FC
- 2007/08: Lincoln FC
- 2008/09: Lincoln FC
- 2009/10: Lincoln FC
- 2010/11: Lincoln FC
- 2011/12: Lincoln FC
- 2012/13: Lincoln Red Imps FC
- 2013/14: Lincoln Red Imps FC
- 2014/15: Lincoln Red Imps FC
- 2015/16: Lincoln Red Imps FC
- 2016/17: Europa FC
- 2017/18: Lincoln Red Imps FC
- 2018/19: Lincoln Red Imps FC
- 2019/20: keiner2
- 2020/21: Lincoln Red Imps FC
- 2021/22: Lincoln Red Imps FC
- 2022/23: Lincoln Red Imps FC
|