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| Year | Sport | Contest | Discipline | Category | Name | Country | Position |
|---|---|---|---|---|---|---|---|
| 1969 | Road Cycling | Vuelta a España | Mountain jersey | Men | Luis Ocaña | Spain | 1 |
| 1968 | Road Cycling | Vuelta a España | Mountain jersey | Men | Francisco Gabica | Spain | 1 |
| 1967 | Road Cycling | Vuelta a España | Mountain jersey | Men | Mariano Díaz | Spain | 1 |
| 1966 | Road Cycling | Vuelta a España | Mountain jersey | Men | Gregorio San Miguel | Spain | 1 |
| 1965 | Road Cycling | Vuelta a España | Mountain jersey | Men | Julio Jimenez | Spain | 1 |
| 1964 | Road Cycling | Vuelta a España | Mountain jersey | Men | Julio Jimenez | Spain | 1 |
| 1963 | Road Cycling | Vuelta a España | Mountain jersey | Men | Julio Jimenez | Spain | 1 |
| 1962 | Road Cycling | Vuelta a España | Mountain jersey | Men | Antonio Karmany | Spain | 1 |
| 1961 | Road Cycling | Vuelta a España | Mountain jersey | Men | Antonio Karmany | Spain | 1 |
| 1960 | Road Cycling | Vuelta a España | Mountain jersey | Men | Antonio Karmany | Spain | 1 |
| 1959 | Road Cycling | Vuelta a España | Mountain jersey | Men | Antonio Suárez | Spain | 1 |
| 1958 | Road Cycling | Vuelta a España | Mountain jersey | Men | Federico Bahamontes | Spain | 1 |
| 1957 | Road Cycling | Vuelta a España | Mountain jersey | Men | Federico Bahamontes | Spain | 1 |
| 1956 | Road Cycling | Vuelta a España | Mountain jersey | Men | Nino Defilippis | Italy | 1 |
| 1955 | Road Cycling | Vuelta a España | Mountain jersey | Men | Giuseppe Buratti | Italy | 1 |
| 1950 | Road Cycling | Vuelta a España | Mountain jersey | Men | Emilio Rodríguez | Spain | 1 |
| 1948 | Road Cycling | Vuelta a España | Mountain jersey | Men | Bernardo Ruiz | Spain | 1 |
| 1947 | Road Cycling | Vuelta a España | Mountain jersey | Men | Emilio Rodríguez | Spain | 1 |
| 1946 | Road Cycling | Vuelta a España | Mountain jersey | Men | Emilio Rodríguez | Spain | 1 |
| 1945 | Road Cycling | Vuelta a España | Mountain jersey | Men | Julián Berrendero | Spain | 1 |
| 1942 | Road Cycling | Vuelta a España | Mountain jersey | Men | Julián Berrendero | Spain | 1 |
| 1941 | Road Cycling | Vuelta a España | Mountain jersey | Men | Fermin Trueba | Spain | 1 |
| 1936 | Road Cycling | Vuelta a España | Mountain jersey | Men | Salvador Molina | Spain | 1 |
| 1935 | Road Cycling | Vuelta a España | Mountain jersey | Men | Edoardo Molinar | Italy | 1 |
| 2025 | Road Cycling | Vuelta a España | Young jersey | Men | Matthew Riccitello | United States | 1 |
| 2024 | Road Cycling | Vuelta a España | Young jersey | Men | Mattias Skjelmose | Denmark | 1 |
| 2023 | Road Cycling | Vuelta a España | Young jersey | Men | Juan Ayuso | Spain | 1 |
| 2022 | Road Cycling | Vuelta a España | Young jersey | Men | Remco Evenepoel | Belgium | 1 |
| 2021 | Road Cycling | Vuelta a España | Young jersey | Men | Gino Mäder | Switzerland | 1 |
| 2020 | Road Cycling | Vuelta a España | Young jersey | Men | Enric Mas | Spain | 1 |
| 2019 | Road Cycling | Vuelta a España | Young jersey | Men | Tadej Pogačar | Slovenia | 1 |
| 2018 | Road Cycling | Vuelta a España | Young jersey | Men | Enric Mas | Spain | 1 |
| 2017 | Road Cycling | Vuelta a España | Young jersey | Men | Miguel Ángel López | Colombia | 1 |
| 2006 | Road Cycling | Volta a Catalunya | Stage race | Men | David Cañada | Spain | 1 |
| 2005 | Road Cycling | Volta a Catalunya | Stage race | Men | Yaroslav Popovych | Ukraine | 1 |
| 2004 | Road Cycling | Volta a Catalunya | Stage race | Men | Miguel Ángel Martín Perdiguero | Spain | 1 |
| 2003 | Road Cycling | Volta a Catalunya | Stage race | Men | José Antonio Pecharromán | Spain | 1 |
| 2002 | Road Cycling | Volta a Catalunya | Stage race | Men | Roberto Heras | Spain | 1 |
| 2001 | Road Cycling | Volta a Catalunya | Stage race | Men | Joseba Beloki | Spain | 1 |
| 2000 | Road Cycling | Volta a Catalunya | Stage race | Men | José María Jiménez | Spain | 1 |
| 1999 | Road Cycling | Volta a Catalunya | Stage race | Men | Manuel Beltrán | Spain | 1 |
| 1998 | Road Cycling | Volta a Catalunya | Stage race | Men | Hernán Buenahora | Colombia | 1 |
| 1997 | Road Cycling | Volta a Catalunya | Stage race | Men | Fernando Escartin | Spain | 1 |
| 1996 | Road Cycling | Volta a Catalunya | Stage race | Men | Alex Zülle | Switzerland | 1 |
| 1995 | Road Cycling | Volta a Catalunya | Stage race | Men | Laurent Jalabert | France | 1 |
| 1994 | Road Cycling | Volta a Catalunya | Stage race | Men | Claudio Chiappucci | Italy | 1 |
| 1993 | Road Cycling | Volta a Catalunya | Stage race | Men | Álvaro Mejía | Colombia | 1 |
| 1992 | Road Cycling | Volta a Catalunya | Stage race | Men | Miguel Induráin | Spain | 1 |
| 1991 | Road Cycling | Volta a Catalunya | Stage race | Men | Miguel Induráin | Spain | 1 |
| 1990 | Road Cycling | Volta a Catalunya | Stage race | Men | Laudelino Cubino | Spain | 1 |
| 1989 | Road Cycling | Volta a Catalunya | Stage race | Men | Marino Lejarreta | Spain | 1 |
| 1988 | Road Cycling | Volta a Catalunya | Stage race | Men | Miguel Induráin | Spain | 1 |
| 1987 | Road Cycling | Volta a Catalunya | Stage race | Men | Álvaro Pino | Spain | 1 |
| 1986 | Road Cycling | Volta a Catalunya | Stage race | Men | Sean Kelly | Ireland | 1 |
| 1985 | Road Cycling | Volta a Catalunya | Stage race | Men | Robert Millar | Great Britain | 1 |
| 1984 | Road Cycling | Volta a Catalunya | Stage race | Men | Sean Kelly | Ireland | 1 |
| 1983 | Road Cycling | Volta a Catalunya | Stage race | Men | Josep Recio | Spain | 1 |
| 1982 | Road Cycling | Volta a Catalunya | Stage race | Men | Alberto Fernández | Spain | 1 |
| 1981 | Road Cycling | Volta a Catalunya | Stage race | Men | Faustino Rupérez | Spain | 1 |
| 1980 | Road Cycling | Volta a Catalunya | Stage race | Men | Marino Lejarreta | Spain | 1 |
| 1979 | Road Cycling | Volta a Catalunya | Stage race | Men | Vicente Belda | Spain | 1 |
| 1978 | Road Cycling | Volta a Catalunya | Stage race | Men | Francesco Moser | Italy | 1 |
| 1977 | Road Cycling | Volta a Catalunya | Stage race | Men | Freddy Maertens | Belgium | 1 |
| 1976 | Road Cycling | Volta a Catalunya | Stage race | Men | Enrique Martínez Heredia | Spain | 1 |
| 1975 | Road Cycling | Volta a Catalunya | Stage race | Men | Fausto Bertoglio | Italy | 1 |
| 1974 | Road Cycling | Volta a Catalunya | Stage race | Men | Bernard Thévenet | France | 1 |
| 1973 | Road Cycling | Volta a Catalunya | Stage race | Men | Domingo Perurena | Spain | 1 |
| 1972 | Road Cycling | Volta a Catalunya | Stage race | Men | Felice Gimondi | Italy | 1 |
| 1971 | Road Cycling | Volta a Catalunya | Stage race | Men | Luis Ocaña | Spain | 1 |
| 1970 | Road Cycling | Volta a Catalunya | Stage race | Men | Franco Bitossi | Italy | 1 |
| 1969 | Road Cycling | Volta a Catalunya | Stage race | Men | Mariano Díaz | Spain | 1 |
| 1968 | Road Cycling | Volta a Catalunya | Stage race | Men | Eddy Merckx | Belgium | 1 |
| 1967 | Road Cycling | Volta a Catalunya | Stage race | Men | Jacques Anquetil | France | 1 |
| 1966 | Road Cycling | Volta a Catalunya | Stage race | Men | Arie den Hartog | Netherlands | 1 |
| 1965 | Road Cycling | Volta a Catalunya | Stage race | Men | Antonio Gómez del Moral | Spain | 1 |
| 1964 | Road Cycling | Volta a Catalunya | Stage race | Men | Joseph Carrara | France | 1 |
| 1963 | Road Cycling | Volta a Catalunya | Stage race | Men | Joseph Novales | France | 1 |
| 1962 | Road Cycling | Volta a Catalunya | Stage race | Men | Antonio Karmany | Spain | 1 |
| 1961 | Road Cycling | Volta a Catalunya | Stage race | Men | Henri Duez | France | 1 |
| 1960 | Road Cycling | Volta a Catalunya | Stage race | Men | Miguel Poblet | Spain | 1 |
| 1959 | Road Cycling | Volta a Catalunya | Stage race | Men | Salvador Botella | Spain | 1 |
| 1958 | Road Cycling | Volta a Catalunya | Stage race | Men | Richard Van Genechten | Belgium | 1 |
| 1957 | Road Cycling | Volta a Catalunya | Stage race | Men | Jesús Loroño | Spain | 1 |
| 1956 | Road Cycling | Volta a Catalunya | Stage race | Men | Aniceto Utset | Spain | 1 |
| 1955 | Road Cycling | Volta a Catalunya | Stage race | Men | José Gómez del Moral | Spain | 1 |
| 1954 | Road Cycling | Volta a Catalunya | Stage race | Men | Walter Serena | Italy | 1 |
| 1953 | Road Cycling | Volta a Catalunya | Stage race | Men | Salvador Botella | Spain | 1 |
| 1952 | Road Cycling | Volta a Catalunya | Stage race | Men | Miguel Poblet | Spain | 1 |
| 1951 | Road Cycling | Volta a Catalunya | Stage race | Men | Primo Volpi | Italy | 1 |
| 1950 | Road Cycling | Volta a Catalunya | Stage race | Men | Antonio Gelabert | Spain | 1 |
| 1949 | Road Cycling | Volta a Catalunya | Stage race | Men | Émile Rol | France | 1 |
| 1948 | Road Cycling | Volta a Catalunya | Stage race | Men | Emilio Rodríguez | Spain | 1 |
| 1947 | Road Cycling | Volta a Catalunya | Stage race | Men | Emilio Rodríguez | Spain | 1 |
| 1946 | Road Cycling | Volta a Catalunya | Stage race | Men | Julián Berrendero | Spain | 1 |
| 1945 | Road Cycling | Volta a Catalunya | Stage race | Men | Bernardo Ruiz | Spain | 1 |
| 1944 | Road Cycling | Volta a Catalunya | Stage race | Men | Miguel Casas | Spain | 1 |
| 1943 | Road Cycling | Volta a Catalunya | Stage race | Men | Julián Berrendero | Spain | 1 |
| 1942 | Road Cycling | Volta a Catalunya | Stage race | Men | Fédérico Ezquerra | Spain | 1 |
| 1941 | Road Cycling | Volta a Catalunya | Stage race | Men | Antonio Andres Sancho | Spain | 1 |
| 1940 | Road Cycling | Volta a Catalunya | Stage race | Men | Christophe Didier | Luxembourg | 1 |
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