Battle in Duklja

After his defeat by the Byzantines at the Spercheios in 995, the Bulgarian tsar Samuel turned his attention to the Serbian and Croatian principalities to the northwest, where Byzantine influence was strong. In 998, he attacked the Serbian principality of Duklja, ruled by Prince Jovan Vladimir.

The Serbs could not withstand the Bulgarian army, and Jovan Vladimir withdrew with his people towards Mount Oblik. When Samuel arrived, he left part of his army to block the Serbs' route and used the remainder to besiege the coastal fortress of Ulcinj. To avoid further bloodshed, the Bulgarians offered Jovan Vladimir the chance to surrender. He initially refused but later realised that his nobles were prepared to betray him and therefore surrendered. Jovan Vladimir was sent into exile at Samuel's palace in Prespa. The Bulgarians then captured Kotor and advanced towards Dubrovnik and Dalmatia.

During his captivity, one of Samuel's daughters, Theodora Kosara, fell in love with the young Serbian prince. Samuel approved their marriage, and Jovan Vladimir was allowed to return to his lands as a Bulgarian official, supervised by the Bulgarian tsar's trusted associate Dragomir. In 1016, however, Jovan Vladimir was killed by the new Bulgarian tsar, Ivan Vladislav, who suspected that Vladimir might be a potential claimant to the throne.