Both countries have predominantly Slavic and Orthodox Christian populations and both officially use the Cyrillic alphabet, but depending on the historical period, their bilateral relations shifted from cooperation to hostility.

Motivated by the common Slavic and Orthodox Christian culture, some people from the region of Macedonia moved to the Russian Empire, where the Macedonian Hussar Regiment was formed.

Also, some notable intellectuals and scholars from the region of Macedonia studied in the Russian Empire, such as: Konstantin Miladinov (1830 – 1862), Krste Misirkov (1874 – 1926) and Dimitrija Čupovski (1878 – 1940).

[1] Russia actively supported the liberation movements in neighbouring Ottoman-ruled Greece, Serbia, Montenegro and Bulgaria, but it declined to do so in the region of Macedonia.

Russia did not support the Ilinden Uprising that took place in the region in 1903 and considered the Mürzsteg reforms a better solution for the problems of the persecuted Christian subjects in Ottoman Macedonia.

As a result of this, the territory of what is now North Macedonia fell under oppressive serbian rule, which continued under the Serbian-dominated Kingdom of Yugoslavia, formed after the First World War.

During the war, Russian troops arrived on the territory of what is now North Macedonia to support their Serbian allies (see: Macedonian front, Monastir offensive and Battle of the Crna Bend).

After the 1917 October Revolution, some white Russian émigrés found refuge in the then Serbian-ruled part of Macedonia, a notable example being the biologist Nikola Nezlobinski (1885 - 1942), known for establishing a natural museum in the city of Struga.

USSR was one of the many countries that provided aid in the form of material and personnel after the Skopje earthquake, that struck the capital of Yugoslav Macedonia on July 26, 1963.

[8] The European Union and NATO delayed North Macedonia's accession for too long[9] and they are perceived by some ethnic Macedonians as positively biased towards the Albanian minority in the country.

The former Russian ambassador Oleg Shcherbak even warned the government of North Macedonia that: "If it came to a conflict between Russia and NATO, you will have the role of a legitimate target".

[14] In 2017, some media claimed that Russian spies and diplomats, together with their supporters from Serbia, have been involved in an effort to spread propaganda and provoke discord in North Macedonia with a goal to stop the country from joining NATO and to pry it away from western influence.

[20][21] On June 5, 2022, North Macedonia closed its airspace for Russia's foreign minister Sergei Lavrov, who planned a meeting in neighbouring Serbia.

[31] Stroitransgaz is owned by Gennady Timchenko, an ally of President Vladimir Putin, who was among the first businessmen to be placed under sanctions by the United States in the annexation of Crimea by the Russian Federation.

[32] Following violent interethnic clashes in the northern city of Kumanovo on 9 May 2015, Russian Foreign Minister Sergei Lavrov accused the West of trying to incite an overthrow of the government of North Macedonia in order to undermine the project.

The government of North Macedonia is working to create good conditions for Russian tourists and in establishing regular airfare between the two countries.