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The Battle of Thessalonica occurred in 995 or earlier, near the city of Thessalonica, Greece. The battle was part of the long Bulgarian–Byzantine war of the late 10th and early 11th centuries. The Bulgarians under their ruler, Tsar Samuil, succeeded in ambushing and destroying the Byzantine garrison of Thessalonica, killing its commander, Gregory Taronites, and capturing his son Ashot.

After the great victory in the Battle of Trajan's Gates, and the subsequent civil war in the Byzantine Empire, Samuil was free to attack the Byzantine strongholds all over the Balkan peninsula. After having secured his rule over most of the northern Balkans, he led a campaign against Thessalonica, Byzantium's second largest city, held by the doux Gregory Taronites.


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