A major battle between the alliance of Georgia and Shirvan and the rising Kara Koyunlu Turkmen near Chalagan (the present day Chalagan-Gyuney, Azerbaijan) in 1412. Timur's campaigns in the Caucasus and Near East in the early 1400s weakened the power of the Ottoman Turks and led to the rise of various tribes. The Kara Koyunlu (Black Sheep) tribal federation was among those benefiting from the political vacuum Timur's campaigns created and the Kara Koyunlu tribesmen, led by a talented Kara Yusuf, did not waste time in seizing control of southern Azerbaijan by 1406. Shervanshah Ibrahim I (1382-1417) of Shirvan (in northern Azerbaijan) was threatened by the Kara Koyunlu expansion, especially after the defection of his former ally, Yar Ahmed Karamanlu of Karabakh. In 1412, Ibrahim appealed for help to King Constantine I of Georgia and, aided by Sidi Ahmed Orlat of Shaki, the Georgian-Shirvani-Shaki alliance troops marched against the Kara Koyunlu. While the size of the armies involved in this battle is unclear, the sources seem to agree that the Georgian detachment consisted of about 2,000 warriors.

The battle was fought near the village Chalagan in December 1412 and resulted in a decisive defeat of the allies. King Constantine and several dozen Georgian troops were captured and beheaded on Kara Yusuf's orders. The battle strengthened the Kara Koyunlu's positions in southern Caucasus and exposed Georgia to the eventual raids by the Turkmen tribesmen.