Olovyannikov's interest in flying began in childhood, and he attended a flying club during his high school studies. Called up for service in the armed forces shortly after the Axis invasion of the Soviet Union in 1941, he was assigned for further training at the Voroshilovgrad military aviation school. Despite only completing 13 of the 150 flying hours usually required, Olovyannikov was quickly pressed into service flying the Ilyushin Il-2 attack aircraft. He was assigned to the , and spent the rest of the war with this unit. His first combat sorties took place during the Battle of Kursk. He went on to see action in many of the important battles as the Red Army advanced through the war, fighting at the Battle of Smolensk, Operation Bagration, the East Prussian offensive, and the Battle of Königsberg. In 1944 he was awarded the title of Hero of the Soviet Union, and ultimately flew 212 sorties, without once being shot down.