Diplomatic relations were established 20 April 1995 by exchange of notes between the Ministry of Foreign Affairs of Ukraine and the Ministry of Foreign Affairs of North Macedonia.

Diplomatic mission of Ukraine in North Macedonia began in June 2000.

Ukraine opened an embassy in the Republic of North Macedonia during November 2001.

As of that year, the Lviv bus plant was the sole supplier of buses to North Macedonia.

It was part of an agreement to expand cooperation between North Macedonia and Ukraine in the fields of culture, education, and science.