Uglješa received the title of caesar when he was a boy from the Emperor Uroš the Weak, and after his father's death most of his lands were usurped by the Dejanović brothers. After the Battle of Rovine in 1395, he probably managed to retake his father's land and became a vassal of the Ottoman Sultan. It is mentioned that at the beginning of the 15th century he gave one church to the Hilandar monastery.