Informal relations started on 9 October 2008 when North Macedonia recognised Kosovo after its declaration of independence from Serbia on 17 February of the same year.

[3][citation needed] This agreement was an important landmark in their diplomatic history since it resolved an eight-year-old border dispute that arose from the 2001 Albanian insurgency in North Macedonia.

[10] Crossing into North Macedonia with Kosovo citizenship requires a valid biometric passport, but national ID cards may also be allowed for certain categories of visitors.

[11] Kosovo and North Macedonia benefit from streamlined processes at border crossings to further facilitate travel between them for mutual tourism and economic cooperation.

[The Republic of Macedonia] would follow the position of NATO and the European Union on Kosovo, but nations in the two organisations have to yet to assume a common stance.

[16] On 27 March 2008, Minister of Foreign Affairs of Macedonia Antonio Milošoski issued the following statement: "In welcoming the constructive position of the Republic of Macedonia concerning Kosovo, the Commission on Foreign Affairs of the European Parliament has expressed concern because of delay in the technical demarcation of the Republic of Macedonia-Kosovo borderline and has asked that this issue be solved in accordance with the Ahtisaari proposal.

[19] Ali Ahmeti, leader of the ethnic Albanian Democratic Union for Integration party, said Macedonia would recognise Kosovo after problems over the border demarcation were resolved.

Bilateral relations between the two neighbouring countries were assessed as good, while the Albanians living in North Macedonia are considered to be a strong connecting bridge with Kosovo.

[25] Kosovo and North Macedonia are deepening economic collaboration, particularly in trade and energy sectors, as part of broader regional development initiatives.

Specifically, in 2024, the bilateral talks pointed to two general areas concerning non-tariff barriers that need to be removed for ease of trade facilitation.

Efforts in these fields are coherent with the region’s economic agenda and with the overall EU vision regarding the capacity of Western Balkan economies to integrate with the community.