Slavic peoples settled in the Balkan region including Macedonia by the late 6th

century. During the 580s, Byzantine literature attests to the Slavs raiding Byza
ntine territories in the region of Macedonia, later aided by 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.[34] Presian's reign apparently coincides with the extension of
Bulgarian control over the Slavic tribes in and around Macedonia. The Slavic peo
ples 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, the Byzantine Emperor Basil II defeated the armies of Tsar Samuil of Bu
lgaria, and within four years the Byzantines restored control over the Balkans (
including Macedonia) for the first time since the 7th century. However, by the l
ate 12th century, Byzantine decline saw the region contested by various politica
l entities, including a brief Norman occupation in the 1080s.
In the early 13th century, a revived Bulgarian Empire gained control of the regi
on. Plagued by political difficulties, the empire did not last, and the region c
ame once again under Byzantine control in the early 14th century. In the 14th ce
ntury, 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 St
efan Dusan's empire.
Following Dusan's death, a weak successor appeared, and power struggles between
nobles divided the Balkans once again. These events 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.
[35] Gradually, all the central Balkans were conquered by the Ottoman Empire and
remained under its domination for five centuries.