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The battle of Messinopolis (Bulgarian: Битка при Месинопол) took place on 4 September 1207 near the town of Komotini (Gyumyurdzhina) in contemporary Greece between the Bulgarians and the Latin Empire. It resulted in a Bulgarian victory.
While the armies of Emperor Kaloyan were besieging Odrin to the east, the King of Solun Boniface of Montferrat launched attacks towards Bulgaria from Serres supported by the Byzantines. His cavalry reached Messinopoplis at 5 days raid to the east of Serres but in the mountainous terrain around the town his army was attacked by a larger force main composed of local Bulgarians. The battle began in the Latin gear guard and Boniface managed to repulse the Bulgarians but while he was chasing them he was killed by an arrow and soon the Crusaders were defeated. His head was sent to Kaloyan who immediately organized a campaign against Boniface's capital Solun. However, Kaloyan was murdered by conspirators during the siege and the grieved Bulgarians raised the siege.