| Games | Athlete/Team | Placement | |
|---|---|---|---|
| 1972 Summer Olympics | Aleksandar Tomov | 2 | Silver |
| 1976 Summer Olympics | Aleksandar Tomov | 2 | Silver |
| 1980 Summer Olympics | Aleksandar Tomov | 2 | Silver |
| 1988 Summer Olympics | Rangel Gerovski | 2 | Silver |
| 1992 Summer Olympics | Rangel Gerovski | AC | |
| 2000 Summer Olympics | Sergei Mureico | 19 | |
| 2004 Summer Olympics | Sergei Mureico | 8 | |
| 2008 Summer Olympics | Ivan Ivanov | 12 | |
| 2024 Summer Olympics | Kiril Milov | 9 |