The Dagestan War (Russian: ), also known as the Invasion of Militants in Dagestan (Russian: ) began when the Chechnya-based Islamic International Peacekeeping Brigade (IIPB), an Islamist group, led by Shamil Basayev, Ibn al-Khattab, Ramzan Akhmadov and Arbi Barayev, invaded the neighboring Russian republic of Dagestan, on 7 August 1999, in support of the Shura of Dagestan separatist rebels. The war ended with a major victory for the Russian Federation and Dagestan Republic, and the retreat of the IIPB. The invasion of Dagestan served as the main casus belli alongside the series of apartment bombings in September 1999 for the Second Chechen War.

The Second Chechen War (Russian: Втора́я чече́нская война́, Chechen: ШолгIа оьрсийн-нохчийн тIом, lit. 'Second Russian-Chechen War') took place in Chechnya and the border regions of the North Caucasus between the Russian Federation and the Chechen Republic of Ichkeria, from August 1999 to April 2009. In August 1999, Islamist fighters from Chechnya infiltrated Russia's Dagestan region, declaring it an independent state and calling for holy war. During the initial campaign, Russian military and pro-Russian Chechen paramilitary forces faced Chechen separatists in open combat and seized the Chechen capital Grozny after a winter siege that lasted from December 1999 until February 2000. Russia established direct rule over Chechnya in May 2000 although Chechen militant resistance throughout the North Caucasus region continued to inflict heavy Russian casualties and challenge Russian political control over Chechnya for several years. Both sides carried out attacks against civilians. These attacks drew international condemnation.

In mid-2000, the Russian government transferred certain military responsibilities to pro-Russian Chechen forces. The military phase of operations was terminated in April 2002, and the coordination of the field operations was given first to the Federal Security Service and then to the Ministry of Internal Affairs in the summer of 2003.

By 2009, Russia had severely disabled the Chechen separatist movement and large-scale fighting ceased. Russian army and Interior Ministry troops ceased patrolling. Grozny underwent reconstruction efforts and much of the city and surrounding areas were rebuilt quickly. Sporadic violence continued throughout the North Caucasus; occasional bombings and ambushes targeting federal troops and forces of the regional governments in the area still occur.In April 2009, the government operation in Chechnya officially ended. As the bulk of the army was withdrawn, the responsibility for dealing with the low-level insurgency was shouldered by the local police force. Three months later, the exiled leader of the separatist government, Akhmed Zakayev, called for a halt to armed resistance against the Chechen police force from August and said he hoped that "starting with this day Chechens will never shoot at each other". This marked the complete end of the Chechen conflict.

The exact death toll of the conflict is unknown. Russian casualties are around 7,500 (official Russian casualty figures) or about 14,000 according to the Committee of Soldiers' Mothers. Unofficial sources estimate a range of 25,000 to 50,000 dead or missing, mostly Chechen civilians.