After completing its formation, the 20th was sent into combat on 20 August as part of the 61st Mixed Aviation Division (SmAD) of the Air Force of the Bryansk Front (VVS), operating from the Alekhina-Mertvoye airfield.

[2] Two days later, a group led by Captain Vasily Dmitrievich Gulyayev downed a German Henschel Hs 126 observation aircraft near Mglin, the regiment's first known victory.

Between 7 November 1942 and 6 March 1943, the regiment was reorganized according to shtat 015/284 and reequipped with newer Yakovlev Yak-7B fighters at the rear airfield of Maksatikha.

From late June, the 86th provided air support for advancing Soviet ground troops during Operation Bagration, the offensive that recaptured Belorussia and eastern Poland.

In the spring of 1945, the regiment fought in the Battle of Königsberg during the East Prussian Offensive, for which it was awarded the Order of Suvorov, 3rd class, on 17 May.

This came at a cost of 120 downed aircraft and 71 pilots killed, divided as follows: 22 in aerial combat, 33 failed to return, 7 in air raids and other non-combat losses, and 9 died in crashes and of wounds.

[2] By the 1980s, in event of a war with NATO, the regiment, as part of the 119th IAD, was to protect infrastructure and military bases in southwestern Ukraine and Moldova from airstrikes.

86th Guards IAP aircraft were nuclear-capable, and according to a different plan, the regiment was to move to bases in Bulgaria and Romania in event of conflict and launch strikes on Turkish airfields with Tactical nuclear weapons from there.

The commander of the 2nd Squadron, Lieutenant Colonel Alexander Gidik, was killed in the crash of his MiG after he lost control near the airfield on 25 May.

With its conversion to the MiG-29, the regiment's mission changed to that of protecting the Black Sea Fleet and its bases, although it was stationed 300 kilometers from the coast.

Most of the regiment's non-Moldovan personnel, including all of its pilots and its commander, Colonel Vladimir Koval, departed for their home countries after its transfer.

[2] These were replaced by Moldovan personnel returning from service in the Soviet Armed Forces, among whom there were not many pilots, even fewer of whom could fly MiG-29s.

During the Transnistria War, on 22 June 1992, a flight of two MiG-29s, Rusu leading and Neburac as wingman, bombed a bridge across the Dniester, connecting Bender and Parcani.

[7] Eventually, a squadron of 16 pilots was formed, but this was not enough for a full-strength regiment, and it was converted into a three-squadron mixed aviation brigade on 16 October 1992.