1991 Azerbaijani Mil Mi-8 shootdown

On November 20, 1991, an Azerbaijani Mil Mi-8 military helicopter, carrying a peacekeeping mission team consisting of 13 Azerbaijani government officials, two Russian and one Kazakhstani Ministry of Internal Affairs officials, three Azerbaijani journalists and three helicopter crew was shot down amidst heavy fighting near the village of Berdashen, also known as Karakend, in Nagorno-Karabakh. All 22 people (19 passengers and three crew) on board were killed in the crash.

Source: Wikipedia — 1991 Azerbaijani Mil Mi-8 shootdown (CC BY-SA 4.0)