| Games | Athlete/Team | Placement | |
|---|---|---|---|
| 1968 Summer Olympics | Nancio Carrillo | =9 | |
| 1972 Summer Olympics | Teófilo Stevenson | 1 | Gold |
| 1976 Summer Olympics | Teófilo Stevenson | 1 | Gold |
| 1980 Summer Olympics | Teófilo Stevenson | 1 | Gold |
| 1992 Summer Olympics | Félix Savón | 1 | Gold |
| 1996 Summer Olympics | Félix Savón | 1 | Gold |
| 2000 Summer Olympics | Félix Savón | 1 | Gold |
| 2004 Summer Olympics | Odlanier Solís | 1 | Gold |
| 2008 Summer Olympics | Osmay Acosta | =3 | Bronze |
| 2012 Summer Olympics | José Larduet | =5 | |
| 2016 Summer Olympics | Erislandy Savón | =3 | Bronze |
| 2020 Summer Olympics | Julio César la Cruz | 1 | Gold |
| 2024 Summer Olympics | Julio César la Cruz | =9 |
