In the Battle of Maritsa of 1371, the King ofLordship of PrilepVukašin 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 the Macedonian region, Marko accepted vassalage under Sultan Murad I to preserve his position. The Battle of Kosovo of 1389 sealed the fate of the region 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 early of the 15th 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 the region of Macedonia became a battleground of Ottoman–Albanian war for more than 20 years, the Ottoman Empire ultimately succeeded in taking the region, incorporating it into Rumelia Eyalet.
Rumelia Eyalet
From its foundation, the province of Rumelia encompassed the entirety of the Ottoman Empire's European possessions. The first capital of Rumelia was probably Edirne, which was also, until the Fall of Constantinople in 1453, the Ottomans' capital city. In the 18th century, Monastir emerged as an alternate residence of the governor, and in 1836, it officially became the capital of the eyalet. At about the same time, the Tanzimat reforms, aimed at modernizing the Empire, split off the new eyalets of Üsküb, Yanya and Selanik and reduced the Rumelia Eyalet to a few provinces around Monastir. The rump eyalet survived until 1867, when, as part of the transition to the more uniform vilayet system, it became part of the Salonica Vilayet. The reduced Rumelia Eyalet, centred at Manastir, encompassed also the sanjaks of Iskenderiyye, Ohri and Kesrye. In 1855, according to the French traveller A. Viquesnel, it comprised the sanjaks of Iskenderiyye, with 7 kazas or sub-provinces, Ohri with 8 kazas, Kesrye with 8 kazas and the pasha-sanjak of Manastir with 11 kazas.
Vilayets
After administrative reform in 1860s, the Ottoman Empire was divided into vilayets which were subdivided into sanjaks.
The northern part of the Macedonian region was included in the Kosovo Vilayet. Sanjaks located in this vilayet that contained territory now within the Republic of North Macedonia were:
Sanjak of Skopje, which included the nahiye of Skopje, Kumanova, İştip, Kratova, and Koçana.
Sanjak of Prizren, which included the nahiye of Kalkandelen.
Monastir Vilayet
The southwestern part of the region was located in the Monastir vilayet. Sanjaks located in this vilayet that contained territory now within the Republic of North Macedonia were:
Sanjak of Monastir, which included Bitola, Ohri, Resne, and Pirlepe
Sanjak of Dibra, which included Debar and Kiçevo
Salonika Vilayet
The southeastern part of the region was located in the Salonika vilayet. Sanjaks located in this vilayet that contained territory now within the Republic of North Macedonia were:
Sanjak of Selanik, which included Tikveş, Usturumca, Köprülü, Doyran, and Gevgili
The Balkan Wars consisted of two wars that occurred in 1912 and 1913. The first began on 8 October 1912 when the nations of the Balkan League, who had large parts of their ethnic populations under Ottoman rule, attacked the Ottoman Empire. It lasted seven months with the Balkan League nations coming up victorious, ending 500 years of Ottoman rule in the Balkans.
Vardar Macedonian cities under Ottoman rule
During the Ottoman rule of the Balkans, cities experienced many changes with regards to the demographic makeup of their population and the look of their cityscapes. With laws that prohibited Christian buildings from being higher than Islamic ones, the skylines of cities like Skopje and Bitola were dominated by minarets. Ottoman traveller Evliya Çelebi visited the city of Bitola in 1661. He wrote that of the seven mosques in the city at the time, six were built in the 16th century. Most of the mosques constructed on the territory of today's Republic of North Macedonia were square in shape with a three-domed portico and a minaret on the building's right side.
