The Sanjak of Kyustendil was an Ottoman administrative-territorial unit that existed from 1395 to 1878. It included the former lands of Konstantin Dragash - Province of the DejanoviÃÂ family.
The Kyustendil Sanjak provided the largest number of Sipahi for the Ottoman army of all European Sanjaks, except Rumelia. In its lands were the Rila Monastery and the town of Veles, North Macedonia.
According to a preserved document, in Kyustendil in 1570 there was a professional chess player.
The Kyustendil Pasha was the first to be mirmiran in the Ottoman Empire because of the glorious military history of the city, notably the Battle of Velbazhd. The title was also awarded because of Konstantin Dragash, who is the grandfather of the last Roman emperor (Constantine XI Dragases Palaiologos) and at the same time the great-great-grandfather of the first Russian tsar (Ivan the Terrible).