Macedonia's first appearance in the contest was in 1998. However, the country had already made efforts to enter the contest two years before at the Eurovision Song Contest 1996's pre-selection round, where it submitted its first song entry, "Samo ti" (Само ти) sung by Kaliopi, which failed to qualify to the final thus eliminating the nation from competing for the first time. Macedonia's efforts to enter the contest were again hindered in 1997, when another new system was introduced where countries with the lowest average scores over the previous four years were excluded from participating.
The country's best result was in 2006, when Elena Risteska sang "Ninanajna" (Нинанајна) in Athens, Greece and came 12th. Macedonia is the only country to have qualified from every semi-final from 2004 to 2007 (other countries have qualified for every final but due to them finishing in the top 10 the previous year, they did not have to compete in the semi-final). Despite never finishing in the top 10, their record of qualifying for every final was only broken in 2008, when the jury vote used in the semi-final chose Sweden as a finalist, despite Tamara, Vrčak and Adrian having come 10th in the televote and not saved by the jury. Since then, only in 2012 Macedonia have made the final. In 2017, they were one of the favorites to win the contest with Jana Burceska and the song "Dance alone", but they only came 15th in the semi final.
Macedonian Radio-Television (MRT), which broadcasts the event, has used the Skopje Fest festival to select the national entry since the country's debut, although it made several changes in the national final format, so the 2004, 2005, 2006, 2007, and 2012 national finals were organised outside the Skopje Festival.
Prior declaring independence in 1991, as a constituent country of SFR Yugoslavia, the Socialist Republic of Macedonia participated in the Yugoslav pre-selection called among the other Yugoslav federal units. Also, Macedonian composers wrote songs for candidates from other parts of Yugoslavia. However, the Macedonian entries never managed to win, and the SR Macedonia was the only federal state never to send a Yugoslav entry to the Eurovision Song Contest. An exception occurred when Maja Odžaklievska won the Yugoslav competition in 1979, but she did not perform in the Eurovision Song Contest 1979 due to the Yugoslavian decision not to participate that year.