Ottoman Vardar Macedonia

Vardar Macedonia, the area that now makes up the Republic of Macedonia, was part of the Ottoman Empire for roughly five hundred years, from 1395 to 1912.

In the Battle of Maritsa of 1371, the King of Lordship of Prilep Vukašin Mrnjavčević and his brother Jovan Uglješa led 70,000 men against the Ottomans. Despite having smaller numbers, the Ottomans managed to kill Vukašin and his brother and win the Battle of Maritsa.

After the battle, most of Serbia broke into smaller principalities. One of those principalities is known as the Kingdom of Prilep, led by Vukašin's son Marko. Like most regional rulers in Macedonia, Marko accepted vassalage under Sultan Murad I to preserve his position.

The Battle of Kosovo of 1389 sealed the fate of Macedonia for the next 500 years. While both armies lost leaders and large numbers of soldiers, the Ottomans could easily assemble another army just as large while the locals could not.

Marko died alongside Konstantin Dragaš at the Battle of Rovine in 1395 and the territory of his realm became the Sanjak of Ohrid.

All of Vardar Macedonia was under Ottoman control by the end of the 14th century, with Skopje falling under Turkish rule on January 19, 1392. Aside from conflict with Skanderbeg's forces, in which areas of western part of Macedonia became a battleground of Ottoman-Albanian war for more than 20 years (1444-1467), the Ottoman Empire ultimately succeeded in taking the region.

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Wikipedia