1916/17: Marítimo

1917/18: Marítimo

1918/19: Não se disputou

1919/20: Não se disputou

1920/21: União

1921/22: Marítimo

1922/23: Marítimo

1923/24: Marítimo

1924/25: Marítimo

1925/26: Marítimo

1926/27: Marítimo

1927/28: União

1928/29: Marítimo

1929/30: Marítimo

1930/31: Marítimo

1931/32: União

1932/33: Marítimo

1933/34: União

1934/35: Nacional

1935/36: Marítimo

1936/37: Nacional

1937/38: União

1938/39: Nacional

1939/40: Marítimo

1940/41: Marítimo

1941/42: Nacional

1942/43: Nacional

1943/44: Nacional

1944/45: Marítimo

1945/46: Marítimo

1946/47: Marítimo

1947/48: Marítimo

1948/49: Marítimo

1949/50: Marítimo

1950/51: Marítimo

1951/52: Marítimo

1952/53: Marítimo

1953/54: Marítimo

1954/55: Marítimo

1955/56: Marítimo

1956/57: União

1957/58: Marítimo

1958/59: União

1959/60: União

1960/61: União

1961/62: União

1962/63: União

1963/64: União

1964/65: União

1965/66: Marítimo

1966/67: Marítimo

1967/68: Marítimo

1968/69: Nacional

1969/70: Marítimo

1970/71: Marítimo

1971/72: Marítimo

1972/73: Marítimo

1973/74: União

1974/75: Nacional

1975/76: Machico

1976/77: Santacruzense

1977/78: União

1978/79: Santacruzense

1979/80: União

1980/81: Portosantense

1981/82: Portosantense

1982/83: Santacruzense

1983/84: Portosantense

1984/85: Portosantense

1985/86: Portosantense

1986/87: Portosantense

1987/88: Portosantense

1988/89: Câmara de Lobos

1989/90: Machico

1990/91: Camacha

1991/92: São Vicente

1992/93: Ribeira Brava

1993/94: Santacruzense

1994/95: 1º de Maio

1995/96: Santana

1996/97: Caniçal

1997/98: Ribeira Brava

1998/99: Pontassolense

1999/00: Choupana

2000/01: Santana

2001/02: Santacruzense

2002/03: Santana

2003/04: Estrela da Calheta

2004/05: Caniçal

2005/06: Canicense

2006/07: Canicense

2007/08: Andorinha

2008/09: União B

2009/10: Santacruzense

2010/11: Bairro da Argentina

2011/12: Xavelhas

2012/13: Câmara de Lobos

2013/14: Pontassolense

2014/15: Caniçal

2015/16: Caniçal