| Games | Athlete/Team | Placement | |
|---|---|---|---|
| 1964 Summer Olympics | Félix Betancourt | =5 | |
| 1968 Summer Olympics | Enrique Regüeiferos | 2 | Silver |
| 1972 Summer Olympics | Andrés Molina | =5 | |
| 1976 Summer Olympics | Andrés Aldama | 2 | Silver |
| 1980 Summer Olympics | José Aguilar | =3 | Bronze |
| 1992 Summer Olympics | Héctor Vinent | 1 | Gold |
| 1996 Summer Olympics | Héctor Vinent | 1 | Gold |
| 2000 Summer Olympics | Diógenes Luna | =3 | Bronze |
| 2004 Summer Olympics | Yudel Johnson | 2 | Silver |
| 2008 Summer Olympics | Roniel Iglesias | =3 | Bronze |
| 2012 Summer Olympics | Roniel Iglesias | 1 | Gold |
| 2016 Summer Olympics | Yasniel Toledo | =5 |
