Damaged apartment buildings in 2006Grozny was once again the epicenter of fighting after the outbreak of the Second Chechen War, which further caused thousands of fatalities. During the early phase of the Russian siege on Grozny in October 25, 1999, Russian forces launched five SS-21 ballistic missiles at the crowded central bazaar and a maternity ward, killing more than 140 people and injuring hundreds. During the massive shelling of the city that followed, most of the Russian artillery were directed toward the upper floors of the buildings; although this caused massive destruction of infrastructure, civilian casualties were much less than in the first battles. The enormous scale of the devastation prompted numerous comparisons with Hiroshima [7] and other cities leveled during World War II.

The final seizure of the city was set in early February 2000, when the Russian military lured the besieged militants to a promised safe passage. Seeing that there was no build-up of forces outside, the militants agreed. One day prior to the planned evacuation, the Russian Army mined the path between the city and the village of Alkhan-Kala and concentrated most firepower on that point. As a result, both the city mayor and military commander were killed; a number of other prominent separatist leaders were also killed or wounded, including Shamil Basayev and several hundred rank-and-file militants. Afterwards, the Russians slowly entered the empty city and on February 6 raised the Russian flag in the centre. Many buildings and even whole areas of the city were systematically dynamited. A month later, it was declared safe to allow the residents to return to their homes, although demolishing continued for some time. In 2003 the United Nations called Grozny the most destroyed city on earth.[8]