| Year | Sport | Medal | Country | Athlete |
| 1896 | Road Cycling
Men's Road Race |  | Greece | Aristidis Konstaninidis |
| 1896 | Road Cycling
Men's Road Race |  | Great Britain | August Goedrich |
| 1896 | Road Cycling
Men's Road Race |  | Great Britain | E. Battel |
| 1906 | Road Cycling
Men's Road Race | | France | Fernand Vast |
| 1906 | Road Cycling
Men's Road Race | | France | Maurice Bardonneau |
| 1906 | Road Cycling
Men's Road Race | | France | Edmond Luguet |
| 1912 | Road Cycling
Men's Individual Time Trial | | South Africa | Rudolph "Okey" Lewis |
| 1912 | Road Cycling
Men's Individual Time Trial | | Great Britain | Frederick Grubb |
| 1912 | Road Cycling
Men's Individual Time Trial | | U.S.A | Carl Schutte |
| 1912 | Road Cycling
Men's Road Race | | South Africa | Rudolph "Okey" Lewis |
| 1912 | Road Cycling
Men's Road Race | | Great Britain | Frederick Grubb |
| 1912 | Road Cycling
Men's Road Race | | U.S.A | Carl Schutte |
| 1920 | Road Cycling
Men's Individual Time Trial | | Sweden | Harry Stenqvist |
| 1920 | Road Cycling
Men's Individual Time Trial | | South Africa | Henry Kaltenbrun |
| 1920 | Road Cycling
Men's Individual Time Trial | | France | Fernand Canteloube |
| 1920 | Road Cycling
Men's Road Race | | Sweden | Harry Stenqvist |
| 1920 | Road Cycling
Men's Road Race | | South Africa | Henry Kaltenbrun |
| 1920 | Road Cycling
Men's Road Race | | France | Fernand Canteloube |
| 1924 | Road Cycling
Men's Individual Time Trial | | France | Armand Blanchonnet |
| 1924 | Road Cycling
Men's Individual Time Trial | | Belgium | Henri Hoevenaers |
| 1924 | Road Cycling
Men's Individual Time Trial | | France | Rene Hamel |
| 1924 | Road Cycling
Men's Road Race | | France | Armand Blanchonnet |
| 1924 | Road Cycling
Men's Road Race | | Belgium | Henri Hoenvenaers |
| 1924 | Road Cycling
Men's Road Race | | France | Rene Hamel |
| 1928 | Road Cycling
Men's Individual Time Trial | | Denmark | Henrik Hansen |
| 1928 | Road Cycling
Men's Individual Time Trial | | Great Britain | Frank Southall |
| 1928 | Road Cycling
Men's Individual Time Trial | | Sweden | Gosta Carlsson |
| 1928 | Road Cycling
Men's Road Race | | Denmark | Hanry Hansen |
| 1928 | Road Cycling
Men's Road Race | | Great Britain | Frank Southall |
| 1928 | Road Cycling
Men's Road Race | | Sweden | Gosta Carlsson |
| 1932 | Road Cycling
Men's Individual Time Trial | | Italy | Attilo Pavesi |
| 1932 | Road Cycling
Men's Individual Time Trial | | Italy | Guglielmo Segato |
| 1932 | Road Cycling
Men's Individual Time Trial | | Sweden | Bernhard Britz |
| 1932 | Road Cycling
Men's Road Race | | Italy | Attilo Pavesi |
| 1932 | Road Cycling
Men's Road Race | | Italy | Guglielmo Segato |
| 1932 | Road Cycling
Men's Road Race | | Sweden | Bernhard Britz |
| 1936 | Road Cycling
Men's Road Race | | France | Robert Charpentier |
| 1936 | Road Cycling
Men's Road Race | | France | Guy Lapebie |
| 1936 | Road Cycling
Men's Road Race | | Switzerland | Ernst Nievergelt |
| 1948 | Road Cycling
Men's Road Race | | France | Jose Beyaert |
| 1948 | Road Cycling
Men's Road Race | | Holland | Gerardus Petrus Voorting |
| 1948 | Road Cycling
Men's Road Race | | Belgium | Lode Wouters |
| 1952 | Road Cycling
Men's Road Race | | Belgium | Andre Noyelle |
| 1952 | Road Cycling
Men's Road Race | | Belgium | Robert Grondelaers |
| 1952 | Road Cycling
Men's Road Race | | Federal Republic of Germany | Edi Ziegler |
| 1956 | Road Cycling
Men's Road Race | | Italy | Ercole Baldini |
| 1956 | Road Cycling
Men's Road Race | | France | Arnaud Geyre |
| 1956 | Road Cycling
Men's Road Race | | Great Britain | Alan Jackson |
| 1960 | Road Cycling
Men's Road Race | | Soviet Union | Viktor Kapitonov |
| 1960 | Road Cycling
Men's Road Race | | Italy | Livio Trape |
| 1960 | Road Cycling
Men's Road Race | | Belgium | Willy van der Berghen |
| 1964 | Road Cycling
Men's Road Race | | Italy | Mario Zanin |
| 1964 | Road Cycling
Men's Road Race | | Denmark | Kjell Akerstrom Rodian |
| 1964 | Road Cycling
Men's Road Race | | Belgium | Walter Godefroot |
| 1968 | Road Cycling
Men's Road Race | | Italy | Pierfranco Vianelli |
| 1968 | Road Cycling
Men's Road Race | | Denmark | Leif Mortensen |
| 1968 | Road Cycling
Men's Road Race | | Sweden | Gosta Petterson |
| 1972 | Road Cycling
Men's Road Race | | Holland | Hennie Kuiper |
| 1972 | Road Cycling
Men's Road Race | | Australia | Keven Clyde Sefton |
| 1972 | Road Cycling
Men's Road Race | | New Zealand | Bruce Biddle |
| 1976 | Road Cycling
Men's Road Race | | Sweden | Bernt Johansson |
| 1976 | Road Cycling
Men's Road Race | | Italy | Giuseppe Martinelli |
| 1976 | Road Cycling
Men's Road Race | | Poland | Mieczyslaw Nowicki |
| 1980 | Road Cycling
Men's Road Race | | Soviet Union | Sergei Sukhoruchenkov |
| 1980 | Road Cycling
Men's Road Race | | Poland | Czeslaw Lang |
| 1980 | Road Cycling
Men's Road Race | | Soviet Union | Yuri Barinov |
| 1984 | Road Cycling
Women's Road Race | | U.S.A | Connie Carpenter-Phinney |
| 1984 | Road Cycling
Women's Road Race | | U.S.A | Rebbeca Twigg |
| 1984 | Road Cycling
Women's Road Race | | Federal Republic of Germany | Sandra Schumacher |
| 1984 | Road Cycling
Men's Road Race | | U.S.A | Alexi Grewal |
| 1984 | Road Cycling
Men's Road Race | | Canada | Steve Bauer |
| 1984 | Road Cycling
Men's Road Race | | Norway | Dag Otto Lauritzen |
| 1988 | Road Cycling
Women's Road Race | | Holland | Monique Knol |
| 1988 | Road Cycling
Women's Road Race | | Federal Republic of Germany | Jutta Niehaus |
| 1988 | Road Cycling
Women's Road Race | | Soviet Union | Laima Zilporite |
| 1988 | Road Cycling
Men's Road Race | | German Democratic Republic | Olaf Ludwig |
| 1988 | Road Cycling
Men's Road Race | | Federal Republic of Germany | Bernd Grone |
| 1988 | Road Cycling
Men's Road Race | | Federal Republic of Germany | Christian Henn |
| 1992 | Road Cycling
Women's Road Race | | Australia | Katherine Watt |
| 1992 | Road Cycling
Women's Road Race | | France | Jeannie Longo-Ciprelli |
| 1992 | Road Cycling
Women's Road Race | | Netherlands | Monique Knol |
| 1992 | Road Cycling
Men's Road Race | | Italy | Fabio Casartelli |
| 1992 | Road Cycling
Men's Road Race | | Netherlands | Erik Dekker |
| 1992 | Road Cycling
Men's Road Race | | Latvia | Dainis Ozols |
| 1996 | Road Cycling
Men's Individual Time Trial | | Spain | Miguel Indurain |
| 1996 | Road Cycling
Men's Individual Time Trial | | Spain | Abraham Olano |
| 1996 | Road Cycling
Men's Individual Time Trial | | Great Britain | Chris Boardman |
| 1996 | Road Cycling
Women's Road Race | | France | Jeannie Longo-Ciprelli |
| 1996 | Road Cycling
Women's Road Race | | Italy | Imelda Chiappa |
| 1996 | Road Cycling
Women's Road Race | | Canada | Clara Hughes |
| 1996 | Road Cycling
Women's Individual Time Trial | | Russia | Zulfiya Zabirova |
| 1996 | Road Cycling
Women's Individual Time Trial | | France | Jeannie Longo-Ciprelli |
| 1996 | Road Cycling
Women's Individual Time Trial | | Canada | Clara Hughes |
| 1996 | Road Cycling
Men's Road Race | | Switzerland | Pascal Richard |
| 1996 | Road Cycling
Men's Road Race | | Denmark | Rolf Sorensen |
| 1996 | Road Cycling
Men's Road Race | | Great Britain | Max Sciandri |
| 2000 | Road Cycling
Men's Individual Time Trial | | Russia | Viacheslav Ekimov |
| 2000 | Road Cycling
Men's Individual Time Trial | | Germany | Jan Ullrich |
| 2000 | Road Cycling
Men's Individual Time Trial | | U.S.A | Lance Armstrong |
| 2000 | Road Cycling
Women's Road Race | | Netherlands | Leontien Zijlaard-Van Moorsel |
| 2000 | Road Cycling
Women's Road Race | | Germany | Hanka Kupfernagel |
| 2000 | Road Cycling
Women's Road Race | | Lithuania | Diana Ziliute |
| 2000 | Road Cycling
Women's Individual Time Trial | | Netherlands | Leontien Zijlaard-Van Moorsel |
| 2000 | Road Cycling
Women's Individual Time Trial | | U.S.A | Mari Holden |
| 2000 | Road Cycling
Women's Individual Time Trial | | France | Jeannie Longo-Ciprelli |
| 2000 | Road Cycling
Men's Road Race | | Germany | Jan Ullrich |
| 2000 | Road Cycling
Men's Road Race | | Kazakhstan | Alexandre Vinokourov |
| 2000 | Road Cycling
Men's Road Race | | Germany | Andreas Kloeden |
| 2004 | Road Cycling
Men's Individual Time Trial | | U.S.A | Tyler Hamilton |
| 2004 | Road Cycling
Men's Individual Time Trial | | Russia | Viacheslav Ekimov |
| 2004 | Road Cycling
Men's Individual Time Trial | | U.S.A | Bobby Julich |
| 2004 | Road Cycling
Women's Road Race | | Australia | Sara Carrigan |
| 2004 | Road Cycling
Women's Road Race | | Germany | Judith Arndt |
| 2004 | Road Cycling
Women's Road Race | | Russia | Olga Slyusareva |
| 2004 | Road Cycling
Women's Individual Time Trial | | Netherlands | Leontien Zijlaard-Van Moorsel |
| 2004 | Road Cycling
Women's Individual Time Trial | | U.S.A | Dede Demet-Barry |
| 2004 | Road Cycling
Women's Individual Time Trial | | Switzerland | Karin Thuerig |
| 2004 | Road Cycling
Men's Road Race | | Italy | Paolo Bettini |
| 2004 | Road Cycling
Men's Road Race | | Portugal | Sergio Paulinho |
| 2004 | Road Cycling
Men's Road Race | | Belgium | Axel Merckx |
| 2008 | Road Cycling
Men's Individual Time Trial | | Switzerland | Fabian Cancellara |
| 2008 | Road Cycling
Men's Individual Time Trial | | Sweden | Gustav Larsson |
| 2008 | Road Cycling
Men's Individual Time Trial | | U.S.A | Levi Leipheimer |
| 2008 | Road Cycling
Women's Road Race | | Great Britain | Nicole Cooke |
| 2008 | Road Cycling
Women's Road Race | | Sweden | Emma Johansson |
| 2008 | Road Cycling
Women's Road Race | | Italy | Tatiana Guderzo |
| 2008 | Road Cycling
Women's Individual Time Trial | | U.S.A | Kristin Armstrong |
| 2008 | Road Cycling
Women's Individual Time Trial | | Great Britain | Emma Pooley |
| 2008 | Road Cycling
Women's Individual Time Trial | | Switzerland | Karin Thurig |
| 2008 | Road Cycling
Men's Road Race | | Spain | Samuel Sanchez |
| 2008 | Road Cycling
Men's Road Race | | Italy | Davide Rebellin |
| 2008 | Road Cycling
Men's Road Race | | Switzerland | Fabian Cancellara |
