| | Rider | Team |
| 1927 |  | Carvalho, Augusto deAugusto de Carvalho (PRT) | Carcavelos |
| 1928 | No race | | |
| 1929 | No race | | |
| 1930 | No race | | |
| 1931 |  | Nicolau, Jose MariaJosé Maria Nicolau (PRT) | Benfica |
| 1932 |  | Trindade, AlfredoAlfredo Trindade (PRT) | Rio de Janeiro |
| 1933 |  | Trindade, AlfredoAlfredo Trindade (PRT) | Sporting Clube de Portugal |
| 1934 |  | Nicolau, Jose MariaJosé Maria Nicolau (PRT) | Benfica |
| 1935 |  | Luis, CesarCésar Luís (PRT) | Leões do Alentejo |
| 1936 | No race | | |
| 1937 | No race | | |
| 1938 |  | Albuquerque, JoseJosé Albuquerque (PRT) | Campo de Ourique |
| 1939 |  | Fernandes, JoaquimJoaquim Fernandes (PRT) | CUF |
| 1940 |  | Albuquerque, JoseJosé Albuquerque (PRT) | Sporting Clube de Portugal |
| 1941 |  | Inacio, FranciscoFrancisco Inácio (PRT) | Sporting Clube de Portugal |
1942– 1945 | No race due to World War II | | |
| 1946 |  | Martins, JoseJosé Martins (PRT) | Iluminante |
| 1947 |  | Martins, JoseJosé Martins (PRT) | Benfica |
| 1948 |  | Moreira, FernandoFernando Moreira (PRT) | FC Porto |
| 1949 |  | Santos, Dias dosDias dos Santos (PRT) | FC Porto |
| 1950 |  | Santos, Dias dosDias dos Santos (PRT) | FC Porto |
| 1951 |  | Barbosa, AlvesAlves Barbosa (PRT) | Sangalhos |
| 1952 |  | Sá, Moreira deMoreira de Sá (PRT) | FC Porto |
| 1953 | No race | | |
| 1954 | No race | | |
| 1955 |  | Silva, Ribeiro daRibeiro da Silva (PRT) | Académico do Porto |
| 1956 |  | Barbosa, AlvesAlves Barbosa (PRT) | Sangalhos |
| 1957 |  | Silva, Ribeiro daRibeiro da Silva (PRT) | Académico do Porto |
| 1958 |  | Barbosa, AlvesAlves Barbosa (PRT) | Sangalhos |
| 1959 |  | Carvalho, CarlosCarlos Carvalho (PRT) | FC Porto |
| 1960 |  | Cardoso, SousaSousa Cardoso (PRT) | FC Porto |
| 1961 |  | Silva, MarioMário Silva (PRT) | FC Porto |
| 1962 |  | Pacheco, JoseJosé Pacheco (PRT) | FC Porto |
| 1963 |  | Roque, JoaoJoão Roque (PRT) | Sporting Clube de Portugal |
| 1964 |  | Leao, JoaquimJoaquim Leão (PRT) | FC Porto |
| 1965 |  | Alves, PeixotoPeixoto Alves (PRT) | Benfica |
| 1966 |  | Valada, FranciscoFrancisco Valada (PRT) | Benfica |
| 1967 |  | Houbrechts, AntoineAntoine Houbrechts (BEL) | Flandria |
| 1968 |  | Silva, AmericoAmérico Silva (PRT) | Benfica |
| 1969 |  | Andrade, JoaquimJoaquim Andrade (PRT) | Sangalhos |
| 1970 |  | Agostinho, JoaquimJoaquim Agostinho (PRT) | Sporting Clube de Portugal |
| 1971 |  | Agostinho, JoaquimJoaquim Agostinho (PRT) | Sporting Clube de Portugal |
| 1972 |  | Agostinho, JoaquimJoaquim Agostinho (PRT) | Sporting Clube de Portugal |
| 1973 |  | Manzaneque, JesusJesus Manzaneque (ESP) | Messias |
| 1974 |  | Mendes, FernandoFernando Mendes (PRT) | Benfica |
| 1975 | No race due to Carnation Revolution | | |
| 1976 |  | Bernardino, FirminoFirmino Bernardino (PRT) | Benfica |
| 1977 |  | Teixeira, AdelinoAdelino Teixeira (PRT) | Lousa |
| 1978 |  | Silva, BelmiroBelmiro Silva (PRT) | Coimbrões |
| 1979 |  | Sousa Santos, JoaquimJoaquim Sousa Santos (PRT) | FC Porto |
| 1980 |  | Miranda, FranciscoFrancisco Miranda (PRT) | Lousa |
| 1981 |  | Zeferino, ManuelManuel Zeferino (PRT) | FC Porto |
| 1982 |  | Chagas, MarcoMarco Chagas (PRT) | FC Porto |
| 1983 |  | Chagas, MarcoMarco Chagas (PRT) | Mako Jeans |
| 1984 |  | Fernandes, VenceslauVenceslau Fernandes (PRT) | Ajacto |
| 1985 |  | Chagas, MarcoMarco Chagas (PRT) | Sporting Clube de Portugal |
| 1986 |  | Chagas, MarcoMarco Chagas (PRT) | Sporting Clube de Portugal |
| 1987 |  | Cunha, ManuelManuel Cunha (PRT) | Sicasal/Torreense |
| 1988 |  | Theakston, CaynCayn Theakston (GBR) | Louletano/Vale do Lobo |
| 1989 |  | Gomes, JoaquimJoaquim Gomes (PRT) | Sicasal/Torreense |
| 1990 |  | Carvalho, FernandoFernando Carvalho (PRT) | Ruquita/Feirense |
| 1991 |  | Silva, JorgeJorge Silva (PRT) | Sicasal/Acral |
| 1992 |  | Freitas, CassioCássio Freitas (BRA) | Recer/Boavista |
| 1993 |  | Gomes, JoaquimJoaquim Gomes (PRT) | Recer/Boavista FCBoavista |
| 1994 |  | Rodrigues, OrlandoOrlando Rodrigues (PRT) | Artiach |
| 1995 |  | Rodrigues, OrlandoOrlando Rodrigues (PRT) | Artiach |
| 1996 |  | Lelli, MassimilianoMassimiliano Lelli (ITA) | Saeco/Levira |
| 1997 |  | Jaskula, ZenonZenon Jaskuła (POL) | Mapei |
| 1998 |  | Serpellini, MarcoMarco Serpellini (ITA) | Brescialat |
| 1999 |  | Plaza, DavidDavid Plaza (ESP) | Benfica (Lisbon)Benfica |
| 2000 |  | Gamito, VitorVítor Gamito (PRT) | Porta da Ravessa |
| 2001 |  | Jeker, FabianFabian Jeker (SUI) | Milaneza/MSS |
| 2002 |  | Moller, ClausClaus Moller (DEN) | Milaneza/MSS |
| 2003 |  | Ribeiro, NunoNuno Ribeiro (PRT) | LA/Pecol |
| 2004 |  | Bernabeu, DavidDavid Bernabéu (ESP) | Milaneza/Maia |
| 2005 |  | Efimkin, VladimirVladimir Efimkin (RUS) | Barloworld |
| 2006 |  | Blanco, DavidDavid Blanco (ESP) | Comunidad Valenciana |
| 2007 |  | Tondo, XavierXavier Tondo (ESP) | LA-MSS |
| 2008 |  | Blanco, DavidDavid Blanco (ESP) | Palmeiras Resort/Tavira |
| 2009 |  | Blanco, DavidDavid Blanco (ESP) | Palmeiras Resort/Prio/Tavira |