Siege of Thessalonica
1383 CE.
Shown on the map at 40.633°, 22.950°.
The first siege of Thessalonica took place between 1383 and 1387 between the Ottoman army dispatched by Murad I and the Byzantine garrison led by Manuel II Palaiologos. After a four-year siege, the city surrendered to the Ottomans.
Text from the Wikipedia article Siege of Thessalonica (1383–1387), licensed CC BY-SA 4.0.