| 2022 |  North Macedonia | Andrea Circles | — | — |
| 2021 | North Macedonia | Vasil Here I Stand | — | — |
| 2020 | North Macedonia | Vasil You | — | — |
| 2019 | North Macedonia | Tamara Todevska Proud | 7 | 305 |
| 2018 | North Macedonia | Eye Cue Lost And Found | — | — |
| 2017 | North Macedonia | Jana Burčeska Dance Alone | — | — |
| 2016 | North Macedonia | Kaliopi Dona | — | — |
| 2015 | North Macedonia | Daniel Kajmakoski Autumn Leaves | — | — |
| 2014 | North Macedonia | Tijana To the Sky | — | — |
| 2013 | North Macedonia | Esma & Lozano Pred Da Se Razdeni | — | — |
| 2012 | North Macedonia | Kaliopi Crno I Belo | 13 | 71 |
| 2011 | North Macedonia | Vlatko Ilievski Rusinka | — | — |
| 2010 | North Macedonia | Gjoko Taneski Jas Ja Imam Silata | — | — |
| 2009 | North Macedonia | Next Time Neshto Shto Ke Ostane | — | — |
| 2008 | North Macedonia | Tamara Todevska Let Me Love You | — | — |
| 2007 | North Macedonia | Karolina Mojot Svet | 14 | 73 |
| 2006 | North Macedonia | Elena Risteska Ninanajna | 12 | 56 |
| 2005 | North Macedonia | Martin Vučić Make My Day | 17 | 52 |
| 2004 | North Macedonia | Toše Proeski Life | 14 | 47 |
| 2002 | North Macedonia | Karolina Od Nas Zavisi | 19 | 25 |
| 2000 | North Macedonia | XXL 100% Te Ljubam | 15 | 29 |
| 1998 | North Macedonia | Vlado Janevski Ne Zori, Zoro | 19 | 16 |
