| Medal | Name | Games | Sport | Event |
|---|
 Gold | Ramón Fonst |  1900 Paris | Fencing | Men's épée |
 Silver | Ramón Fonst | 1900 Paris | Fencing | Men's amateurs-masters épée |
| Gold | Ramón Fonst |  1904 St. Louis | Fencing | Men's épée |
| Gold | Ramón Fonst | 1904 St. Louis | Fencing | Men's foil |
| Gold | Manuel Díaz | 1904 St. Louis | Fencing | Men's sabre |
| Gold | Albertson Van Zo Post | 1904 St. Louis | Fencing | Men's singletick |
| Silver | Charles Tatham | 1904 St. Louis | Fencing | Men's épée |
| Silver | Albertson Van Zo Post | 1904 St. Louis | Fencing | Men's foil |
 Bronze | Charles Tatham | 1904 St. Louis | Fencing | Men's foil |
| Bronze | Albertson Van Zo Post | 1904 St. Louis | Fencing | Men's épée |
| Bronze | Albertson Van Zo Post | 1904 St. Louis | Fencing | Men's sabre |
| Silver | Carlos de Cárdenas |  1948 London | Sailing | Men's star class |
| Silver | Enrique Figuerola |  1964 Tokyo | Athletics | Men's 100 metres |
| Silver | Enrique Figuerola
Pablo Montes
Juan Morales
Hermes Ramirez |  1968 Mexico City | Athletics | Men's 4 × 100 metre relay |
| Silver | Miguelina Cobián
Marlene Elejarde
Violetta Quesada
Fulgencia Romay | 1968 Mexico City | Athletics | Women's 4 × 100 metre relay |
| Silver | Rolando Garbey | 1968 Mexico City | Boxing | Men's light middleweight |
| Silver | Enrique Regüeiferos | 1968 Mexico City | Boxing | Men's light welterweight |
| Gold | Orlando Martínez |  1972 Munich | Boxing | Men's bantamweight |
| Gold | Emilio Correa | 1972 Munich | Boxing | Men's welterweight |
| Gold | Teófilo Stevenson | 1972 Munich | Boxing | Men's heavyweight |
| Silver | Gilberto Carrillo | 1972 Munich | Boxing | Men's light heavyweight |
| Bronze | Silvia Chivás | 1972 Munich | Athletics | Women's 100 metres |
| Bronze | Silvia Chivás
Marlene Elejarde
Fulgencia Romay
Carmen Valdés | 1972 Munich | Athletics | Women's 4 × 100 metre relay |
| Bronze | Men's basketball team | 1972 Munich | Basketball | Men's team |
| Bronze | Douglas Rodríguez | 1972 Munich | Boxing | Men's flyweight |
| Gold | Alberto Juantorena |  1976 Montreal | Athletics | Men's 400 metres |
| Gold | Alberto Juantorena | 1976 Montreal | Athletics | Men's 800 metres |
| Gold | Ángel Herrera | 1976 Montreal | Boxing | Men's featherweight |
| Gold | Teófilo Stevenson | 1976 Montreal | Boxing | Men's heavyweight |
| Gold | Jorge Hernández | 1976 Montreal | Boxing | Men's light flyweight |
| Gold | Héctor Rodríguez | 1976 Montreal | Judo | Men's lightweight |
| Silver | Alejandro Casañas | 1976 Montreal | Athletics | Men's 110m hurdles |
| Silver | Ramón Duvalón | 1976 Montreal | Boxing | Men's flyweight |
| Silver | Sixto Soria | 1976 Montreal | Boxing | Men's light heavy weight |
| Silver | Andrés Aldama | 1976 Montreal | Boxing | Men's light welterweight |
| Bronze | Rolando Garbey | 1976 Montreal | Boxing | Men's light middleweight |
| Bronze | Luis Martínez | 1976 Montreal | Boxing | Men's middleweight |
| Bronze | Men's volleyball team | 1976 Montreal | Volleyball | Men's team competition |
| Gold | María Caridad Colón |  1980 Moscow | Athletics | Women's javelin throw |
| Gold | Juan Hernández | 1980 Moscow | Boxing | Men's bantamweight |
| Gold | Teófilo Stevenson | 1980 Moscow | Boxing | Men's heavyweight |
| Gold | Armando Martínez | 1980 Moscow | Boxing | Men's light middleweight |
| Gold | Ángel Herrera | 1980 Moscow | Boxing | Men's lightweight |
| Gold | José Gómez Mustelier | 1980 Moscow | Boxing | Men's middleweight |
| Gold | Andrés Aldama | 1980 Moscow | Boxing | Men's welterweight |
| Gold | Daniel Núñez | 1980 Moscow | Weightlifting | Men's bantamweight (-56 kg) |
| Silver | Silvio Leonard | 1980 Moscow | Athletics | Men's 100 metres |
| Silver | Alejandro Casañas | 1980 Moscow | Athletics | Men's 110 metres |
| Silver | Adolfo Horta | 1980 Moscow | Boxing | Men's featherweight |
| Silver | Hipólito Ramos | 1980 Moscow | Boxing | Men's light flyweight |
| Silver | Jose Rodríguez | 1980 Moscow | Judo | Men's extra lightweight (60 kg) |
| Silver | Juan Ferrer | 1980 Moscow | Judo | Men's half middleweight (78 kg) |
| Silver | Isaac Azcuy | 1980 Moscow | Judo | Men's middleweight (86 kg) |
| Bronze | Luis Delis | 1980 Moscow | Athletics | Men's discus throw |
| Bronze | Ricardo Rojas | 1980 Moscow | Judo | Men's light heavyweight |
| Bronze | José Aguilar | 1980 Moscow | Boxing | Men's light welterweight |
| Bronze | Roberto Castrillo | 1980 Moscow | Shooting | Men's skeet shooting |
| Bronze | Alberto Blanco | 1980 Moscow | Weightlifting | Men's 100 kg |
| Gold | Javier Sotomayor |  1992 Barcelona | Athletics | Men's high jump |
| Gold | Maritza Martén | 1992 Barcelona | Athletics | Women's discus throw |
| Gold | Cuba national baseball team | 1992 Barcelona | Baseball | Baseball |
| Gold | Joel Casamayor | 1992 Barcelona | Boxing | Men's bantamweight |
| Gold | Félix Savón | 1992 Barcelona | Boxing | Men's heavyweight |
| Gold | Rogelio Marcelo | 1992 Barcelona | Boxing | Men's light flyweight |
| Gold | Juan Carlos Lemus | 1992 Barcelona | Boxing | Men's light middleweight |
| Gold | Héctor Vinent | 1992 Barcelona | Boxing | Men's light welterweight |
| Gold | Ariel Hernández | 1992 Barcelona | Boxing | Men's middleweight |
| Gold | Roberto Balado | 1992 Barcelona | Boxing | Men's super heavyweight |
| Gold | Odalis Revé | 1992 Barcelona | Judo | Women's middleweight (66 kg) |
| Gold | Women's volleyball team | 1992 Barcelona | Volleyball | Women's team competition |
| Gold | Héctor Milián | 1992 Barcelona | Wrestling (Greco-Roman) | Men's Greco-Roman light heavyweight |
| Gold | Alejandro Puerto | 1992 Barcelona | Wrestling (Freestyle) | Men's freestyle bantamweight (57 kg) |
| Silver | Roberto Hernández
Héctor Herrera
Lázaro Martínez
Norberto Téllez | 1992 Barcelona | Athletics | Men's 4 × 400 metre relay |
| Silver | Raúl González | 1992 Barcelona | Boxing | Men's flyweight |
| Silver | Juan Hernández | 1992 Barcelona | Boxing | Men's welterweight |
| Silver | Guillermo Betancourt
Tulio Díaz
Hermenegildo García
Oscar García
Elvis Gregory | 1992 Barcelona | Fencing | Men's foil team |
| Silver | Estela Rodríguez | 1992 Barcelona | Judo | Women's heavyweight |
| Silver | Pablo Lara | 1992 Barcelona | Weightlifting | Men's middleweight (75 kg) |
| Bronze | Jorge Aguilera
Joel Isasi
Joel Lamela
Andrés Simón | 1992 Barcelona | Athletics | Men's 4 × 100 metre relay |
| Bronze | Roberto Moya | 1992 Barcelona | Athletics | Men's discus throw |
| Bronze | Ana Fidelia Quirot | 1992 Barcelona | Athletics | Women's 800 metres |
| Bronze | Ioamnet Quintero | 1992 Barcelona | Athletics | Women's high jump |
| Bronze | Elvis Gregory | 1992 Barcelona | Fencing | Men's foil |
| Bronze | Israel Hernández | 1992 Barcelona | Judo | Men's half lightweight (65 kg) |
| Bronze | Amarilis Savón | 1992 Barcelona | Judo | Women's extra lightweight (48 kg) |
| Bronze | Driulis González | 1992 Barcelona | Judo | Women's lightweight (56 kg) |
| Bronze | Wilber Sánchez | 1992 Barcelona | Wrestling (Greco-Roman) | Men's Greco-Roman light flyweight |
| Bronze | Juan Marén | 1992 Barcelona | Wrestling (Greco-Roman) | Men's Greco-Roman featherweight |
| Bronze | Lázaro Reinoso | 1992 Barcelona | Wrestling (Freestyle) | Men's freestyle featherweight (62 kg) |
| Gold | Cuba national baseball team | 1996 Atlanta | Baseball | Baseball |
| Gold | Maikro Romero | 1996 Atlanta | Boxing | Men's flyweight |
| Gold | Félix Savón | 1996 Atlanta | Boxing | Men's heavyweight |
| Gold | Héctor Vinent | 1996 Atlanta | Boxing | Men's light welterweight |
| Gold | Ariel Hernández | 1996 Atlanta | Boxing | Men's middleweight |
| Gold | Driulis González | 1996 Atlanta | Judo | Women's lightweight (56 kg) |
| Gold | Women's volleyball team | 1996 Atlanta | Volleyball | Women's team competition |
| Gold | Pablo Lara | 1996 Atlanta | Weightlifting | Men's middleweight (76 kg) |
| Gold | Filiberto Azcuy | 1996 Atlanta | Wrestling (Greco-Roman) | Men's Greco-Roman welterweight (74 kg) |
| Silver | Ana Fidelia Quirot | 1996 Atlanta | Athletics | Women's 800 metres |
| Silver | Arnaldo Mesa | 1996 Atlanta | Boxing | Men's bantamweight |
| Silver | Alfredo Duvergel | 1996 Atlanta | Boxing | Men's middleweight |
| Silver | Juan Hernández Sierra | 1996 Atlanta | Boxing | Men's welterweight |
| Silver | Iván Trevejo | 1996 Atlanta | Fencing | Men's épée |
| Silver | Estela Rodríguez | 1996 Atlanta | Judo | Women's heavyweight |
| Silver | Rodolfo Falcón | 1996 Atlanta | Swimming | Men's 100m backstroke |
| Silver | Juan Marén | 1996 Atlanta | Wrestling (Greco-Roman) | Men's Greco-Roman featherweight (62 kg) |
| Bronze | Yoelbi Quesada | 1996 Atlanta | Athletics | Men's triple jump |
| Bronze | Oscar García
Elvis Gregory
Rolando Tucker | 1996 Atlanta | Fencing | Men's foil team |
| Bronze | Israel Hernández | 1996 Atlanta | Judo | Men's half lightweight (65 kg) |
| Bronze | Amarilis Savón | 1996 Atlanta | Judo | Women's extra lightweight (48 kg) |
| Bronze | Legna Verdecia | 1996 Atlanta | Judo | Women's half lightweight (52 kg) |
| Bronze | Diadenis Luna | 1996 Atlanta | Judo | Women's half heavyweight (72 kg) |
| Bronze | Neisser Bent | 1996 Atlanta | Swimming | Men's 100m backstroke |
| Bronze | Alexis Vila | 1996 Atlanta | Wrestling (Freestyle) | Men's freestyle paperweight (48 kg) |
| Gold | Anier García |  2000 Sydney | Athletics | Men's 110m hurdles |
| Gold | Iván Pedroso | 2000 Sydney | Athletics | Men's long jump |
| Gold | Guillermo Rigondeaux | 2000 Sydney | Boxing | Men's bantamweight |
| Gold | Félix Savón | 2000 Sydney | Boxing | Men's heavyweight |
| Gold | Mario Kindelán | 2000 Sydney | Boxing | Men's lightweight |
| Gold | Jorge Gutiérrez | 2000 Sydney | Boxing | Men's middleweight |
| Gold | Legna Verdecia | 2000 Sydney | Judo | Women's 52 kg |
| Gold | Sibelis Veranes | 2000 Sydney | Judo | Women's 70 kg |
| Gold | Ángel Matos | 2000 Sydney | Taekwondo | Men's 80 kg |
| Gold | Women's volleyball team | 2000 Sydney | Volleyball | Women's team competition |
| Gold | Filiberto Azcuy | 2000 Sydney | Wrestling (Greco-Roman) | Men's Greco-Roman |
| Silver | Javier Sotomayor | 2000 Sydney | Athletics | Men's high jump |
| Silver | Cuba national baseball team | 2000 Sydney | Baseball | Baseball |
| Silver | Ledis Balceiro | 2000 Sydney | Canoeing | Men's C-1 1000m |
| Silver | Leobaldo Pereira
Ibrahim Rojas | 2000 Sydney | Canoeing | Men's C-2 1000m |
| Silver | Driulis González | 2000 Sydney | Judo | Women's 57 kg |
| Silver | Daima Beltrán | 2000 Sydney | Judo | Women's +78 kg |
| Silver | Urbia Melendez | 2000 Sydney | Taekwondo | Women's 49 kg |
| Silver | Yoel Romero | 2000 Sydney | Wrestling (Freestyle) | Men's freestyle 85 kg |
| Silver | Lázaro Rivas | 2000 Sydney | Wrestling (Greco-Roman) | Men's Greco-Roman 54 kg |
| Silver | Juan Marén | 2000 Sydney | Wrestling (Greco-Roman) | Men's Greco-Roman 63 kg |
| Bronze | José Ángel César
Iván García
Freddy Mayola
Luis Alberto Pérez-Rionda | 2000 Sydney | Athletics | Men's 4 × 100 m |
| Bronze | Osleidys Menéndez | 2000 Sydney | Athletics | Women's javelin throw |
| Bronze | Maikro Romero | 2000 Sydney | Boxing | Men's light flyweight |
| Bronze | Diógenes Luña | 2000 Sydney | Boxing | Men's light welterweight |
| Bronze | Nelson Loyola
Carlos Pedroso
Iván Trevejo | 2000 Sydney | Fencing | Men's team épée |
| Bronze | Manolo Poulot | 2000 Sydney | Judo | Men's 60 kg |
| Bronze | Alexis Rodríguez | 2000 Sydney | Wrestling (Freestyle) | Men's freestyle 130 kg |
| Gold | Osleidys Menéndez |  2004 Athens | Athletics | Women's javelin throw |
| Gold | Yumileidi Cumbá | 2004 Athens | Athletics | Women's shot put |
| Gold | Cuba national baseball team | 2004 Athens | Baseball | Baseball |
| Gold | Guillermo Rigondeaux | 2004 Athens | Boxing | Men's bantamweight |
| Gold | Yuriorkis Gamboa | 2004 Athens | Boxing | Men's flyweight |
| Gold | Odlanier Solís | 2004 Athens | Boxing | Men's heavyweight |
| Gold | Yan Bartelemí | 2004 Athens | Boxing | Men's light flyweight |
| Gold | Mario Kindelan | 2004 Athens | Boxing | Men's lightweight |
| Gold | Yandro Miguel Quintana | 2004 Athens | Wrestling (Freestyle) | Men's 55–60 kg |
| Silver | Yipsi Moreno | 2004 Athens | Athletics | Women's hammer throw |
| Silver | Yudel Johnson Cedeno | 2004 Athens | Boxing | Men's 60–64 kg |
| Silver | Lorenzo Aragon | 2004 Athens | Boxing | Men's 64–69 kg |
| Silver | Ledis Balceiro
Ibrahim Rojas | 2004 Athens | Canoeing | Men's C-2 500m |
| Silver | Daima Beltran | 2004 Athens | Judo | Women's heavyweight |
| Silver | Yanelis Labrada | 2004 Athens | Taekwondo | Women's -49 kg |
| Silver | Roberto Monzon | 2004 Athens | Wrestling (Greco-Roman) | Men's 55–60 kg |
| Bronze | Cuba national volleyball team | 2004 Athens | Volleyball | Women's competition |
| Bronze | Anier García | 2004 Athens | Athletics | Men's 110m hurdles |
| Bronze | Yunaika Crawford | 2004 Athens | Athletics | Women's hammer throw |
| Bronze | Michel Lopez Nunez | 2004 Athens | Boxing | Men's super heavyweight |
| Bronze | Yordanis Arencibia | 2004 Athens | Judo | Men's half-lightweight |
| Bronze | Yurisel Laborde | 2004 Athens | Judo | Women's half-heavyweight |
| Bronze | Amarilis Savón | 2004 Athens | Judo | Women's half-lightweight |
| Bronze | Driulys González | 2004 Athens | Judo | Women's half-middleweight |
| Bronze | Yurisleidy Lupetey | 2004 Athens | Judo | Women's lightweight |
| Bronze | Juan Miguel Rodríguez | 2004 Athens | Shooting | Men's skeet (125 targets) |
| Bronze | Iván Fundora | 2004 Athens | Wrestling (Freestyle) | Men's 66–74 kg |
| Gold | Dayron Robles |  2008 Beijing | Athletics | Men's 110m hurdles |
| Gold | Mijain López | 2008 Beijing | Wrestling (Greco-Roman) | Men's 120 kg |
| Gold | Yipsi Moreno | 2008 Beijing | Athletics | Women's hammer throw |
| Silver | Cuba national baseball team | 2008 Beijing | Baseball | Baseball |
| Silver | Yankiel León | 2008 Beijing | Boxing | Men's Bantamweight |
| Silver | Andry Laffita | 2008 Beijing | Boxing | Men's flyweight |
| Silver | Emilio Correa | 2008 Beijing | Boxing | Men's middleweight |
| Silver | Carlos Banteux | 2008 Beijing | Boxing | Men's welterweight |
| Silver | Yoanka González | 2008 Beijing | Cycling (Track) | Women's points race |
| Silver | Yanet Bermoy | 2008 Beijing | Judo | Women's -48 kg |
| Silver | Anaysi Hernández | 2008 Beijing | Judo | Women's -70 kg |
| Silver | Yalennis Castillo | 2008 Beijing | Judo | Women's -78 kg |
| Bronze | Ibrahim Camejo | 2008 Beijing | Athletics | Men's long jump |
| Bronze | Leonel Suárez | 2008 Beijing | Athletics | Men's decathlon |
| Bronze | Yampier Hernández | 2008 Beijing | Boxing | Men's light flyweight |
| Bronze | Yordenis Ugás | 2008 Beijing | Boxing | Men's lightweight |
| Bronze | Osmai Acosta Duarte | 2008 Beijing | Boxing | Men's heavyweight |
| Bronze | Roniel Iglesias | 2008 Beijing | Boxing | Men's light welterweight |
| Bronze | Yordanis Arencibia | 2008 Beijing | Judo | Men's -66 kg |
| Bronze | Óscar Brayson | 2008 Beijing | Judo | Men's +100 kg |
| Bronze | Idalys Ortiz | 2008 Beijing | Judo | Women's +78 kg |
| Bronze | Eglis Yaima Cruz | 2008 Beijing | Shooting | Women's 50m rifle 3 positions |
| Bronze | Daynellis Montejo | 2008 Beijing | Taekwondo | Women's 49 kg |
| Bronze | Yordanis Borrero | 2008 Beijing | Weightlifting | Men's 69 kg |
| Bronze | Jadier Valladares | 2008 Beijing | Weightlifting | Men's 85 kg |
| Bronze | Yoandry Hernández | 2008 Beijing | Weightlifting | Men's 94 kg |
| Gold | Robeisy Ramírez | 2012 London | Boxing | Men's flyweight |
| Gold | Roniel Iglesias | 2012 London | Boxing | Men's lightweight |
| Gold | Idalys Ortiz | 2012 London | Judo | Women's +78 kg |
| Gold | Leuris Pupo | 2012 London | Shooting | Men's 25m rapid fire pistol |
| Gold | Mijain López | 2012 London | Wrestling (Greco-Roman) | Men's 120 kg |
| Silver | Yarisley Silva | 2012 London | Athletics | Women's pole vault |
| Silver | Asley González | 2012 London | Judo | Men's -90 kg |
| Silver | Yanet Bermoy | 2012 London | Judo | Women's -52 kg |
| Bronze | Leonel Suárez | 2012 London | Athletics | Men's decathlon |
| Bronze | Lázaro Álvarez | 2012 London | Boxing | Men's bantamweight |
| Bronze | Yasniel Toledo | 2012 London | Boxing | Men's lightweight |
| Bronze | Robelis Despaigne | 2012 London | Taekwondo | Men's +80 kg |
| Bronze | Iván Cambar | 2012 London | Weightlifting | Men's 77 kg |
| Bronze | Liván López | 2012 London | Wrestling (Freestyle) | Men's 66 kg freestyle |
| Gold | Robeisy Ramírez |  2016 Rio de Janeiro | Boxing | Men's bantamweight |
| Gold | Julio César La Cruz | 2016 Rio de Janeiro | Boxing | Men's light heavyweight |
| Gold | Arlen López | 2016 Rio de Janeiro | Boxing | Men's middleweight |
| Gold | Ismael Borrero | 2016 Rio de Janeiro | Wrestling (Greco-Roman) | Men's 59 kg |
| Gold | Mijaín López | 2016 Rio de Janeiro | Wrestling (Greco-Roman) | Men's 130 kg |
| Silver | Idalys Ortiz | 2016 Rio de Janeiro | Judo | Women's +78 kg |
| Silver | Yasmany Lugo | 2016 Rio de Janeiro | Wrestling (Greco-Roman) | Men's 98 kg |
| Bronze | Denia Caballero | 2016 Rio de Janeiro | Athletics | Women's discus throw |
| Bronze | Joahnys Argilagos | 2016 Rio de Janeiro | Boxing | Men's light flyweight |
| Bronze | Lázaro Álvarez | 2016 Rio de Janeiro | Boxing | Men's lightweight |
| Bronze | Erislandy Savón | 2016 Rio de Janeiro | Boxing | Men's heavyweight |
| Gold | Luis Orta | 2020 Tokyo | Wrestling | Men's Greco-Roman 60 kg |
| Gold | Mijaín López | 2020 Tokyo | Wrestling | Men's Greco-Roman 130 kg |
| Gold | Fernando Jorge
Serguey Torres | 2020 Tokyo | Canoeing | Men's C-2 1000 metres |
| Gold | Roniel Iglesias | 2020 Tokyo | Boxing | Men's welterweight |
| Gold | Arlen López | 2020 Tokyo | Boxing | Men's light heavyweight |
| Gold | Julio César La Cruz | 2020 Tokyo | Boxing | Men's heavyweight |
| Gold | Andy Cruz | 2020 Tokyo | Boxing | Men's lightweight |
| Silver | Idalys Ortiz | 2020 Tokyo | Judo | Women's +78 kg |
| Silver | Juan Miguel Echevarría | 2020 Tokyo | Athletics | Men's long jump |
| Silver | Leuris Pupo | 2020 Tokyo | Shooting | Men's 25 metre rapid fire pistol |
| Bronze | Rafael Alba | 2020 Tokyo | Taekwondo | Men's +80 kg |
| Bronze | Maykel Massó | 2020 Tokyo | Athletics | Men's long jump |
| Bronze | Yaime Pérez | 2020 Tokyo | Athletics | Women's discus throw |
| Bronze | Lázaro Álvarez | 2020 Tokyo | Boxing | Men's featherweight |
| Bronze | Reineris Salas | 2020 Tokyo | Wrestling | Men's freestyle 97 kg |
