Theodosius of Skopje was born as Vasil Iliev Gologanov (Bulgarian & Macedonian: Васил Илиев Гологанов) in the then Bulgarian populated village of Tarlis (now part of Kato Nevrokopi, Greece) in the Ottoman Empire.
His brother Ivan Gologanov was a collector of folk songs, most famous for editing the book Veda Slovena.
Vasil studied in the classical Greek gymnasium in Serres.
In 1862 Theodosius became a monk in the monastery of Saint John Prodromus near Serres, and later was ordained as a hierodeacon from the Greek Patriarch of Constantinople.
Sometime in 1867 he left for Hercegovina, where he worked as a protosingel of Metropolitan Prokopius.
After he came back to Bulgarian lands in 1868, Theodosius became a priest in Plovdiv and then in Krichim.

When the Bulgarian Exarchate was established in 1870 he joined it, but soon under the pressure from the Greek Patriarch of Constantinople he renounced the Exarchate.
However, in 1874 after the Christian population of the bishoprics of Skopje and Ohrid voted overwhelmingly in favour of joining the Exarchate, Theodossius repentеd and the Bulgarian Holy Synod restored him to communion.
Between 1874 and 1875 Theodosius was the head of the local Bulgarian Orthodox Church organization in the region of Serres.
He was ordained as an archmandrite in 1875 and became an assistant of the Metropolitan of Nish, who at the time was under the jurisdiction of the Bulgarian Exarch.
Between 1878 and 1880 Archimandrite Theodosius was in Istanbul and performed the duties of Exarch Joseph I, since the exarch was stuck in Plovdiv after the start of the Russo-Turkish War.

Theodosius continued to hold high ranking positions within the Exarchate and in 1885 he was chosen as a bishop of the episcopacy of Skopje but under the pressure of the Ecumenical Patriarch of Constantinople the Sultan issued official ordinance only in 1890.
Meanwhile, in 1887 he met with Kosta Grupchev and Nahum Evrov, agents of Stojan Novakovic, representatives of the so-called Association of Serbo-Macedonians.
As a result of these meetings during this time, Theodosius came under the influence of the ideas of Macedonism.
Afterwards, as a bishop of Skopje, Theodosius renounced de facto again the Bulgarian Exarchate and attempted to restore the Archbishopric of Ohrid and to separate the episcopacies in Macedonia from the Bulgarian Exarchate.
His plans were to create a Macedonian Uniat Church with help from Bishop of Rome, but they failed soon and he was fired from the Exarchate in 1892 because of his separatism.
According to Simeon Radev, bishop Theodosius' separatism stemmed from his personal hatred of Exarch Joseph I. Petko Slaveykov 
believed Teodosius Macedonism was inspired by the Greek propaganda and in fact his activity was favorably regarded by pro-Greek activists.
Most of the Macedonian specialists on the history of the Macedonian Orthodox Church, consider that the religious separatism of Theodosius represented indeed a form of early Macedonian nationalism.

He was banished from the Exarchate and exiled in a monastery near Sofia.
However, later Theodosius repented again and accepted as before a pro-Bulgarian position on the Macedonian Question.
As result he was rehabilitated and between 1901 and 1906 served as bishop of the Plovdiv eparchy.
During 1913 he participated on the Christianization of the Pomaks in the Rhodopes, a mission held from the Bulgarian Exarhate and IMORO.
Bishop Theodosius also led the short-lived eparchy of Gyumyurdzhina, (Komotini) between 1915 and 1919, when the area was part of Bulgaria.

Since 1910 Theodosius Gologanov was a member of the Bulgarian Academy of Sciences, he wrote articles on religion and translated into Bulgarian some of the works of Virgil, François-René de Chateaubriand, John Milton and others.
In one of his articles, published in the newspaper "Mir", he first claimed that the  forefather of the Bulgarian National Revival, Saint Paisius of Hilendar had been born in Bansko, Pirin Macedonia.
Theodosius of Skopje was born as Vasil Iliev Gologanov (Bulgarian & Macedonian: Васил Илиев Гологанов) in the then Bulgarian populated village of Tarlis (now part of Kato Nevrokopi, Greece) in the Ottoman Empire. His brother Ivan Gologanov was a collector of folk songs, most famous for editing the book Veda Slovena. Vasil studied in the classical Greek gymnasium in Serres. In 1862 Theodosius became a monk in the monastery of Saint John Prodromus near Serres, and later was ordained as a hierodeacon from the Greek Patriarch of Constantinople. Sometime in 1867 he left for Hercegovina, where he worked as a protosingel of Metropolitan Prokopius. After he came back to Bulgarian lands in 1868, Theodosius became a priest in Plovdiv and then in Krichim.
When the Bulgarian Exarchate was established in 1870 he joined it, but soon under the pressure from the Greek Patriarch of Constantinople he renounced the Exarchate. However, in 1874 after the Christian population of the bishoprics of Skopje and Ohrid voted overwhelmingly in favour of joining the Exarchate, Theodossius repentеd and the Bulgarian Holy Synod restored him to communion. Between 1874 and 1875 Theodosius was the head of the local Bulgarian Orthodox Church organization in the region of Serres. He was ordained as an archmandrite in 1875 and became an assistant of the Metropolitan of Nish, who at the time was under the jurisdiction of the Bulgarian Exarch. Between 1878 and 1880 Archimandrite Theodosius was in Istanbul and performed the duties of Exarch Joseph I, since the exarch was stuck in Plovdiv after the start of the Russo-Turkish War.
Theodosius continued to hold high ranking positions within the Exarchate and in 1885 he was chosen as a bishop of the episcopacy of Skopje but under the pressure of the Ecumenical Patriarch of Constantinople the Sultan issued official ordinance only in 1890. Meanwhile, in 1887 he met with Kosta Grupchev and Nahum Evrov, agents of Stojan Novakovic, representatives of the so-called Association of Serbo-Macedonians. As a result of these meetings during this time, Theodosius came under the influence of the ideas of Macedonism. Afterwards, as a bishop of Skopje, Theodosius renounced de facto again the Bulgarian Exarchate and attempted to restore the Archbishopric of Ohrid and to separate the episcopacies in Macedonia from the Bulgarian Exarchate. His plans were to create a Macedonian Uniat Church with help from Bishop of Rome, but they failed soon and he was fired from the Exarchate in 1892 because of his separatism. According to Simeon Radev, bishop Theodosius' separatism stemmed from his personal hatred of Exarch Joseph I. Petko Slaveykov 
believed Teodosius Macedonism was inspired by the Greek propaganda and in fact his activity was favorably regarded by pro-Greek activists. Most of the Macedonian specialists on the history of the Macedonian Orthodox Church, consider that the religious separatism of Theodosius represented indeed a form of early Macedonian nationalism.
He was banished from the Exarchate and exiled in a monastery near Sofia. However, later Theodosius repented again and accepted as before a pro-Bulgarian position on the Macedonian Question. As result he was rehabilitated and between 1901 and 1906 served as bishop of the Plovdiv eparchy. During 1913 he participated on the Christianization of the Pomaks in the Rhodopes, a mission held from the Bulgarian Exarhate and IMORO. Bishop Theodosius also led the short-lived eparchy of Gyumyurdzhina, (Komotini) between 1915 and 1919, when the area was part of Bulgaria.
Since 1910 Theodosius Gologanov was a member of the Bulgarian Academy of Sciences, he wrote articles on religion and translated into Bulgarian some of the works of Virgil, François-René de Chateaubriand, John Milton and others. In one of his articles, published in the newspaper "Mir", he first claimed that the  forefather of the Bulgarian National Revival, Saint Paisius of Hilendar had been born in Bansko, Pirin Macedonia.
Theodosius of Skopje