1996 Summer Olympics |
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| Kayak Singles, Slalom, Men | Lazar Popovski | 29 | |
| Canadian Singles, Slalom, Men | Nenad Trpovski | 30 | |
| Kayak Singles, Slalom, Women | Ana Ugrinovska | 29 | |
2000 Summer Olympics |
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| Kayak Singles, Slalom, Men | Lazar Popovski | 17 | |
2004 Summer Olympics |
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| Kayak Singles, Slalom, Men | Lazar Popovski | 16 | |
2008 Summer Olympics |
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| Kayak Singles, Slalom, Men | Atanas Nikolovski | 19 |