Ottoman-era Republic of Macedonia

During the 580s, Byzantine literature attests to the Slavs raiding Byzantine territories in the region of Macedonia, aided by Avars or Bulgars. Historical records document that in c.680 a group of Bulgars, Slavs and Byzantines led by a Bulgar called Kuber settled in the region of Keramisian plain, centred on the city of Bitola.[16] Presian's reign apparently coincides with the extension of Bulgarian control over the Slavic tribes in and around Macedonia. The Slavic peoples that settled in the region of Macedonia accepted Christianity as their own religion around the 9th century, during the reign of Tsar Boris I of Bulgaria.

In 1014, Emperor Basil II finally defeated the armies of Tsar Samuil of Bulgaria and by 1018 the Byzantines restored control over Macedonia (and all of the Balkans) for the first time since the 7th century. However, by the late 12th century, Byzantine decline saw the region contested by various political entities, including a brief Norman occupation in the 1080s.

In the early 13th century, a revived Bulgarian Empire gained control of the region. Plagued by political difficulties the empire did not last and the region came once again under Byzantine control in early 14th century. In the 14th century, it became part of the Serbian Empire, who saw themselves as liberators of their Slavic kin from Byzantine despotism. Skopje became the capital of Tsar Stefan Dusan's empire.

With Dusan's death, a weak successor appeared and power struggles between nobles divided the Balkans once again. This coincided with the entry of the Ottoman Turks into Europe. The Kingdom of Prilep was one of the short lived states that emerged from the collapse of the Serbian Empire in the 14th century.[17] With no major Balkan power left to defend Christianity, central Balkans fell to Turkish rule — and remained under it for five centuries.

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