| Games | Athlete/Team | Placement | |
|---|---|---|---|
| 1964 Summer Olympics | Fermín Espinosa | =5 | |
| 1968 Summer Olympics | Fermín Espinosa | =17 | |
| 1972 Summer Olympics | Orlando Martínez | 1 | Gold |
| 1976 Summer Olympics | Orlando Martínez | =9 | |
| 1980 Summer Olympics | Juan Hernández Pérez | 1 | Gold |
| 1992 Summer Olympics | Joel Casamayor | 1 | Gold |
| 1996 Summer Olympics | Arnaldo Mesa | 2 | Silver |
| 2000 Summer Olympics | Guillermo Rigondeaux | 1 | Gold |
| 2004 Summer Olympics | Guillermo Rigondeaux | 1 | Gold |
| 2008 Summer Olympics | Yankiel León | 2 | Silver |
| 2012 Summer Olympics | Lázaro Álvarez | =3 | Bronze |
| 2016 Summer Olympics | Robeisy Ramírez | 1 | Gold |
