| Games | Athlete/Team | Placement | |
|---|---|---|---|
| 1992 Summer Olympics | Héctor Milián | 1 | Gold |
| 1996 Summer Olympics | Héctor Milián | 5 | |
| 2000 Summer Olympics | Reynaldo Peña | 15 | |
| 2004 Summer Olympics | Ernesto Peña | 4 | |
| 2012 Summer Olympics | Yunior Estrada | =5 | |
| 2016 Summer Olympics | Yasmany Lugo | 2 | Silver |
| 2020 Summer Olympics | Gabriel Rosillo | 13 | |
| 2024 Summer Olympics | Gabriel Rosillo | =3 | Bronze |