He fell at the Battle of Rovine (17 May 1395), serving the Ottomans against Wallachia, fighting alongside Serbian magnates Stefan Lazarević and Marko Mrnjavčević.

In 1395, together with his neighbor and ally, the Serbian king of Prilep Marko, Konstantin Dragaš was killed fighting for their Ottoman overlord Sultan Bayezid I against Mircea cel Bătrân of Wallachia at Rovine, near Craiova.

The name of his first wife is unknown, but she is not identical with Thamar (Tamara), the daughter of the Emperor (tsar) Ivan Alexander of Bulgaria, who had married a certain despotēs Constantine.

[6] Usually depicted as an overraly negative character, his characterisation primarily serves as a contrast to the persona of Marko Kraljević (the two are often portrayed as being blood brothers), with a purpose of emphasising the difference between the two seemingly identical natures of their respective relations with the Ottomans, since both were the latter's vassals.

Whereas Marko is portrayed as accepting the Ottoman suzeranity for the sake and the well-being of his flock, Konstantin seeks a way to preserve his position and privileges with little to no regard to any form of higher moral code.