| 1927 |  | Augusto de Carvalho (PRT) | Carcavelos |
1928
1930 | No race |
| 1931 | | José Maria Nicolau (PRT) | Benfica |
| 1932 | | Alfredo Trindade (PRT) | Rio de Janeiro |
| 1933 | | Alfredo Trindade (PRT) | Sporting |
| 1934 | | José Maria Nicolau (PRT) | Benfica |
| 1935 | | César Luís (PRT) | Leões do Alentejo |
1936
1937 | No race |
| 1938 | | José Albuquerque (PRT) | Campo de Ourique |
| 1939 | | Joaquim Fernandes (PRT) | CUF |
| 1940 | | José Albuquerque (PRT) | Sporting |
| 1941 | | Francisco Inácio (PRT) | Sporting |
1942–
1945 | No race due to World War II |
| 1946 | | José Martins (PRT) | Iluminante |
| 1947 | | José Martins (PRT) | Benfica |
| 1948 | | Fernando Moreira (PRT) | FC Porto |
| 1949 | | Dias dos Santos (PRT) | FC Porto |
| 1950 | | Dias dos Santos (PRT) | FC Porto |
| 1951 | | Alves Barbosa (PRT) | Sangalhos |
| 1952 | | Moreira de Sá (PRT) | FC Porto |
| 1953 | No race |
| 1954 | No race |
| 1955 | | Ribeiro da Silva (PRT) | Académico do Porto |
| 1956 | | Alves Barbosa (PRT) | Sangalhos |
| 1957 | | Ribeiro da Silva (PRT) | Académico do Porto |
| 1958 | | Alves Barbosa (PRT) | Sangalhos |
| 1959 | | Carlos Carvalho (PRT) | FC Porto |
| 1960 | | Sousa Cardoso (PRT) | FC Porto |
| 1961 | | Mário Silva (PRT) | FC Porto |
| 1962 | | José Pacheco (PRT) | FC Porto |
| 1963 | | João Roque (PRT) | Sporting |
| 1964 | | Joaquim Leão (PRT) | FC Porto |
| 1965 | | Peixoto Alves (PRT) | Benfica |
| 1966 | | Francisco Valada (PRT) | Benfica |
| 1967 |  | Antoine Houbrechts (BEL) | Flandria |
| 1968 | | Américo Silva (PRT) | Benfica |
| 1969 | | Joaquim Andrade (PRT) | Sangalhos |
| 1970 | | Joaquim Agostinho (PRT) | Sporting |
| 1971 | | Joaquim Agostinho (PRT) | Sporting |
| 1972 | | Joaquim Agostinho (PRT) | Sporting |
| 1973 |  | Jesus Manzaneque (ESP) | Messias |
| 1974 | | Fernando Mendes (PRT) | Benfica |
| 1975 | No race due to Carnation Revolution |
| 1976 | | Firmino Bernardino (PRT) | Benfica |
| 1977 | | Adelino Teixeira (PRT) | Lousa |
| 1978 | | Belmiro Silva (PRT) | Coimbrões |
| 1979 | | Joaquim Sousa Santos (PRT) | FC Porto |
| 1980 | | Francisco Miranda (PRT) | Lousa |
| 1981 | | Manuel Zeferino (PRT) | FC Porto |
| 1982 | | Marco Chagas (PRT) | FC Porto |
| 1983 | | Marco Chagas (PRT) | Mako Jeans |
| 1984 | | Venceslau Fernandes (PRT) | Ajacto |
| 1985 | | Marco Chagas (PRT) | Sporting |
| 1986 | | Marco Chagas (PRT) | Sporting |
| 1987 | | Manuel Cunha (PRT) | Sicasal/Torreense |
| 1988 |  | Cayn Theakston (GBR) | Louletano/Vale do Lobo |
| 1989 | | Joaquim Gomes (PRT) | Sicasal/Torreense |
| 1990 | | Fernando Carvalho (PRT) | Ruquita/Feirense |
| 1991 | | Jorge Silva (PRT) | Sicasal/Acral |
| 1992 |  | Cássio Freitas (BRA) | Recer/Boavista |
| 1993 | | Joaquim Gomes (PRT) | Recer/Boavista FCBoavista |
| 1994 | | Orlando Rodrigues (PRT) | Artiach |
| 1995 | | Orlando Rodrigues (PRT) | Artiach |
| 1996 |  | Massimiliano Lelli (ITA) | Saeco/Levira |
| 1997 |  | Zenon Jaskuła (POL) | Mapei |
| 1998 | | Marco Serpellini (ITA) | Brescialat |
| 1999 |  | David Plaza (ESP) | Benfica |
| 2000 | | Vítor Gamito (PRT) | Porta da Ravessa |
| 2001 |  | Fabian Jeker (SUI) | Milaneza-MSS |
| 2002 |  | Claus Michael Møller (DEN) | Milaneza-MSS |
| 2003 | | Nuno Ribeiro (PRT) | LA-Pecol |
| 2004 | | David Bernabéu (ESP) | Milaneza-Maia |
| 2005 |  | Vladimir Efimkin (RUS) | Team Barloworld-Valsir |
| 2006 | | David Blanco (ESP) | Comunidad Valenciana |
| 2007 | | Xavier Tondo (ESP) | LA-MSS |
| 2008 | | David Blanco (ESP) | Palmeiras Resort-Tavira |
| 2009 | | David Blanco (ESP) | Palmeiras Resort-Prio |
| 2010 | | David Blanco (ESP) | Palmeiras Resort-Prio |
| 2011 | | Ricardo Mestre (PRT) | Tavira-Prio |
| 2012 | | David Blanco (ESP) | Efapel–Glassdrive |
| 2013 | | Alejandro Marque (ESP) | OFM-Quinta da Lixa |
| 2014 | | Gustavo César Veloso (ESP) | OFM-Quinta da Lixa |
| 2015 | | Gustavo César Veloso (ESP) | W52-Quinta da Lixa |
| 2016 | | Rui Vinhas (POR) | W52-FC Porto-Porto Canal |
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