The then-Republic of Macedonia joined the Partnership for Peace in 1995 and commenced its Membership Action Plan in 1999 at the Washington Summit, at the same time as eight other countries (Albania, Bulgaria, Estonia, Latvia, Lithuania, Romania, Slovenia, Slovakia).

[6] Greece counterargued that it was a collective decision of NATO not to invite the Republic of Macedonia, and therefore the interim accord signed between the two countries was not violated.

Some analysts, such as Jorge Benitez of the Atlantic Council think tank, argued that this reluctance was partly due to the new security climate after Russia's annexation of Crimea.

[10] In March 2016, Macedonian Defense Minister Zoran Jolevski stated his hope that his country's handling of the 2015 European migrant crisis might bring it closer to NATO membership.

[2] Macedonian Prime Minister Zoran Zaev, speaking alongside NATO Secretary-General Jens Stoltenberg in Skopje on 3 June 2019, said that he expected the ratification process to be finalised by the end of October.

[15] By that time North Macedonia was expected to join NATO in early 2020, with the alliance publicly reassuring the country its accession would go ahead.

[16] North Macedonia was given a seat at the 2019 London summit alongside other NATO members and was represented by a delegation headed by Prime Minister Zoran Zaev.

[20][21][22] On 9 December 2021, a ceremony was held at Skopje Airport to mark the inclusion of North Macedonia in the NATO Air Policing system.

[101] A majority of the population of the Republic of Macedonia criticised the government stance and opposed NATO intervention in Kosovo due to fears over irredentism from ethnic Albanians within the country, the unstable economy, disruption of trade brought about by war, and Slavic solidarity with Serbs.

[102] Prime Minister Ljubčo Georgievski stated during the war that anti-NATO sentiment was the "second biggest threat" to the country after the arrival of Albanian refugees from Kosovo.