| YEAR WINNER | CLUB | WINNING TEAM||
|---|---|---|---|
| 1927 | Augusto Carvalho | Carcavelos | Carcavelos |
| 1931 | José María Nicolau | Benfica | Benfica |
| 1932 | Alfredo Trindade | Rio de Janeiro | Benfica |
| 1933 | Alfredo Trindade | Sporting | Sporting |
| 1934 | José María Nicolau | Benfica | Benfica |
| 1935 | César Luís | Leões Alentejo | Campo de Ourique |
| 1938 | José Albuquerque | Campo de Ourique | CUF |
| 1939 | Joaquim Fernandes | CUF | Benfica |
| 1940 | José Albuquerque | Sporting | Sporting |
| 1941 | Francisco Inácio | Sporting | Sporting |
| 1946 | José Martins | Iluminante | Iluminante |
| 1947 | José Martins | Benfica | Benfica |
| 1948 | Fernando Moreira | FC Porto | FC Porto |
| 1949 | Días dos Santos | FC Porto | FC Porto |
| 1950 | Días dos Santos | FC Porto | FC Porto |
| 1951 | Alves Barbosa | Sangalhos | Sangalhos |
| 1952 | Moreira de Sá | FC Porto | FC Porto |
| 1955 | Ribeiro da Silva | Académico FC | FC Porto |
| 1956 | Alves Barbosa | Sangalhos | Académico FC |
| 1957 | Ribeiro da Silva | Académico FC | Académico FC |
| 1958 | Alves Barbosa | Sangalhos | FC Porto |
| 1959 | Carlos Carvalho | FC Porto | Licor 43 |
| 1960 | Sousa Cardoso | FC Porto | FC Porto |
| 1961 | Mário Silva | FC Porto | Sporting |
| 1962 | José Pacheco | FC Porto | Sporting |
| 1963 | João Roque | Sporting | Benfica |
| 1964 | Joaquim Leão | FC Porto | FC Porto |
| 1965 | Peixoto Alves | Benfica | Flândria |
| 1966 | Francisco Valada | Benfica | Benfica |
| 1967 | Tony Houbrechts | Flândria | Sporting |
| 1968 | Américo Silva | Benfica | Sporting |
| 1969 | Joaquim Andrade | Sangalhos | FC Porto |
| 1970 | Joaquim Agostinho | Sporting | Sporting |
| 1971 | Joaquim Agostinho | Sporting | Sporting |
| 1972 | Joaquim Agostinho | Sporting | Sporting |
| 1973 | Jesús Manzaneque | Messias | Sporting |
| 1974 | Fernando Mendes | Benfica | Benfica |
| 1976 | Firmino Bernardino | Benfica | sangalhos |
| 1977 | Adelino Teixeira | Lousa | Águias de Alpiarça |
| 1978 | Belmiro Silva | Coimbrões | Lousa |
| 1979 | Joaquim S. Santos | FC Porto | FC Porto |
| 1980 | Francisco Miranda | Lousa | FC Porto |
| 1981 | Manuel Zeferino | FC Porto | FC Porto |
| 1982 | Marco Chagas | FC Porto | Bombarralense |
| 1983 | Marco Chagas | Mako Jeans | Rodovil-Ajacto |
| 1984 | Venceslau Fernandes | Ajacto | Sporting |
| 1985 | Marco Chagas | Sporting | Sporting |
| 1986 | Marco Chagas | Sporting | Lousa |
| 1987 | Manuel Cunha | Sicasal/Torreense | Sicasal/Torreense |
| 1988 | Cayn Theakston | Louletano/V. Lobo | Louletano/V. Lobo |
| 1989 | Joaquim Gomes | Sicasal/Torreense | Recer/Boavista |
| 1990 | Fernando Carvalho | Ruquita/Feirense | Sicasal/Acral |
| 1991 | Jorge Silva | Sicasal/Acral | Sicasal/Acral |
| 1992 | Cassio Freitas | Recer/Boavista | Sicasal/Acral |
| 1993 | Joaquim Gomes | Recer/Boavista | Artiach Royal |
| 1994 | Orlando Rodrigues | Artiach | Artiach |
| 1995 | Orlando Rodrigues | Artiach | Sicasal/Acral |
| 1996 | Massimiliano Lelli | Saeco | Maia |
| 1997 | Zenon Jaskula | Mapei | Recer/Boavista |
| 1998 | Marco Serpellini | Brescialat | Festina |
| 1999 | David Plaza | Benfica | Benfica |
| 2000 | Vítor Gamito | Porta da Ravessa | Porta da Ravessa |
| 2001 | Fabian Jeker | Milaneza MSS | Porta da Ravessa |
| 2002 | Claus Moller | Milaneza MSS | Milaneza MSS |
| 2003 | Nuno Ribeiro | LA - Pecol | Milaneza MSS |
| 2004 | David Bernabéu | Milaneza MSS | Milaneza MSS |
| 2005 | Vladimir Efimkin | Team Barloworld | Com. Valenciana |
| 2006 | David Blanco | Com. Valenciana | LA / LIberty Seguros |
| 2007 | Xavier Tondo | LA-MSS | Liberty Seguros |
| 2008 | David Blanco | Palmeiras Resort / Tav | Liberty Seguros |
| 2009 | David Blanco | Palmeiras R.T. | Palmeiras R.T. |
| 2010 | David Blanco | Palmeiras R.T. | Barbot Siper |
| 2011 | Ricardo Mestre | Tavira Prio | Tavira Prio |
| 2012 | David Blanco | Efapel / Glassdrive | Efapel / Glassdrive |
| 2013 | Alejandro Marque | OFM / Q.da Lixa | Efapel / Glassdrive |
| 2014 | Gustavo Veloso | OFM / Q.da Lixa | OFM / Q.da Lixa |
| 2015 | Gustavo Veloso | W52-Q. da Lixa | OFM / Q.da Lixa |
| 2016 | Rui Vinhas | W52 FC Porto | W52 FC Porto |
| *2017 | ---------- | ---------- | ---------- |
| **2018 | ---------- | ---------- | ---------- |
| 2019 | João Rodrigues | W52 fC Porto | W52 FC Porto |
| 2020 | Amaro Antunes | W52 FC Porto | W52 FC Porto |
| ***2021 | ---------- | ---------- | ---------- |
| 2022 | Maurício Moreira | Glassdrive / Q8 Anicolor | Glassdrive / Q8 Anicolor |
| 2023 | Colin Stussi | Team Vorarlberg | Glassdrive / Q8 Anicolor |
| 2024 | Artem Nych | Sabgal / Anicolor | Sabgal / Anicolor |
| 2025 | Artem Nych | Anicolor - Tien 21Anicolor - Tien 21 |
*/**/*** No official winner was declared for the years 2017, 2018 and 2021 due to the sanctions imposed by the UCI on Spanish rider Raúl Alarcón and Protuguese rides Amaro Antunes, which affected those years.