Siege of Cyropolis
328 BCE.
Shown on the map at 36.773°, 66.874°.
Cyropolis was the largest of seven towns in the region that Alexander the Great targeted for conquest in 329 BC. His goal was the conquest of Sogdiana. Alexander first sent Craterus to Cyropolis, the largest of the Sogdian towns holding out against Alexander's forces. Craterus' instructions were to "take up a position close to the town, surround it with a ditch and stockade, and then assemble such siege engines as might suit his purpose". The idea was to keep the inhabitants focused on their own defences and to prevent them from sending assistance out to the other towns. Starting from Gazza, Alexander went on to conquer the other surrounding towns. Five of the seven towns were taken in two days. Many of the inhabitants were killed. Alexander then arrived at Cyropolis, which was the best fortified of the towns and had the largest population. It also had reputedly the best fighters of the region. Alexander battered Cyropolis' defences with the siege engines. While the bombardment went on, Alexander ordered certain of his troops to sneak through a dried-up water course that went under the town's wall.
Text from the Wikipedia article Siege of Cyropolis, licensed CC BY-SA 4.0.