The country had previously attempted to join the contest in 1996 but failed to qualify from the pre-selection round. The capital of the landlocked country is Skopje. Until 2019, the country participated under the name F.Y.R. Macedonia.
| Event | Contestant | Song | Place | |
|---|---|---|---|---|
| Birmingham 1998 | Vlado Janevski |
Ne Zori, Zoro
|
16 points 19th | |
| Stockholm 2000 | XXL |
100\% Te Ljubam
|
29 points 15th | |
| Tallinn 2002 | Karolina |
Od Nas Zavisi
|
25 points 19th | |
| Istanbul 2004 | Tose Proeski |
Life
|
||
| 71 points 10th | ||||
| 47 points 14th | ||||
| Kyiv 2005 | Martin Vucic |
Make My Day
|
||
| 97 points 9th | ||||
| 52 points 17th | ||||
| Athens 2006 | Elena Risteska |
Ninanajna
|
||
| 76 points 10th | ||||
| 56 points 12th | ||||
| Helsinki 2007 | Karolina | |||
| 97 points 9th | ||||
| 73 points 14th | ||||
| Belgrade 2008 | Tamara, Vrčak & Adrijan |
Let Me Love You
|
||
| 64 points 11th | ||||
| Moscow 2009 |
Next Time
|
Neshto Shto Ke Ostane
|
||
| 45 points 10th | ||||
| Oslo 2010 |
Gjoko Taneski
|
Jas Ja Imam Silata
|
||
| 37 points 15th | ||||
| Düsseldorf 2011 |
Vlatko Ilievski
|
Rusinka
|
||
| 36 points 16th | ||||
| Baku 2012 |
Kaliopi
|
|||
| 53 points 9th | ||||
| 71 points 13th | ||||
| Malmö 2013 |
Esma & Lozano
|
|||
| 28 points 16th | ||||
| Copenhagen 2014 |
Tijana
|
|||
| 33 points 13th | ||||
| Vienna 2015 |
Daniel Kajmakoski
|
Autumn Leaves
|
||
| 28 points 15th | ||||
| Stockholm 2016 |
Kaliopi
|
Dona
|
||
| 88 points 11th | ||||
| Kyiv 2017 |
Jana Burčeska
|
Dance Alone
|
||
| 69 points 15th | ||||
| Lisbon 2018 |
Eye Cue
|
|||
| 24 points 18th | ||||
| Tel Aviv 2019 |
Tamara Todevska
|
|||
| 239 points 2nd | ||||
| 305 points 7th | ||||
North Macedonia
Birmingham 1998
Stockholm 2000
Tallinn 2002
Istanbul 2004
Kyiv 2005
Athens 2006
Helsinki 2007
Belgrade 2008
Moscow 2009
Oslo 2010
Düsseldorf 2011
Baku 2012
Malmö 2013
Copenhagen 2014
Vienna 2015
Stockholm 2016
Kyiv 2017
Lisbon 2018
Tel Aviv 2019
