Although he was named Metropolitan Bishop of the Bulgarian Exarchate in Skopje, he is known for his failed attempt to establish a separate Macedonian Church as a restoration of the Archbishopric of Ohrid.

Theodosius of Skopje was born as Vasil Iliev Gologanov (Bulgarian and Macedonian: Васил Илиев Гологанов)[4] on 7 January 1846 in the then Slavic populated village of Tarlis (now part of Kato Nevrokopi municipality, Greece) in the Ottoman Empire.

[2] In 1862 he became a monk under the name of Theodosius in the monastery of Saint John Prodromus near Serres,[2] and later was ordained as a hierodeacon from the Greek Patriarch of Constantinople.

In Plovdiv (1867 – 1878), he contacted famous Bulgarian National Revival activists such as Yoakim Gruev, Nayden Gerov and Dragan Manchov.

Later Theodosius was released with the assistance of the Greek Metropolitan, and due to the strong pressure to be set free, he renounced the Exarchate.

[10] However, in the same year, after the Christian population of the bishoprics of Skopje and Ohrid voted overwhelmingly in favour of joining the Exarchate, Theodosius repentеd and the Bulgarian Holy Synod restored him to communion.

[11][non-primary source needed] Between 1874 and 1875 Theodosius was the head of the local Bulgarian Orthodox Church organization in the region of Serres.

[17][non-primary source needed] During 1913 he participated on the Christianization of the Pomaks in the Rhodopes, a mission held from the Bulgarian Exarhate and IMORO.

During this period he served in Sofia, where in November 1915, when the Bulgarian army defeated Serbian troops in Macedonia, he performed a solemn prayer on the occasion of the Victory Day.

He wrote articles on religion and translated into Bulgarian some of the works of Virgil, François-René de Chateaubriand, John Milton and others.