Siege of Samarkand
1494 CE.
Shown on the map at 39.654°, 66.960°.
The sieges of Samarkand (1494-1496) were two failed sieges of Samarkand during the chaotic years of civil war that preceded the fall of the Timurid Empire in 1501.
Text from the Wikipedia article Siege of Samarkand (1490s), licensed CC BY-SA 4.0.