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Uglješa married Jelena (later nun Jefimija), daughter of Vojihna, the Caesar of Drama.[3][4] This boosted the power of Uglješa, who would later govern the region alongside his father-in-law.[4] Vojihna died in ca 1360, and his lands were inherited by Uglješa.[5]
He was given the title of despotes by the widowed Serbian empress, Helena of Bulgaria, in 1365. His domain was situated along the lower course of the Struma with Serres as seat, eventually replacing Helena in its possession. From 1368, his territory was under the religious jurisdiction of the Ecumenical Patriarchate of Constantinople. The Patriarch mentioned the master of Raška (another name for Serbia), Jovan Uglješa, in a letter from 1371.