He graduated from a junior officers' school in Irkutsk and fought in World War I as a platoon commander in the 8th Company of the 56th Infantry Regiment of the Russian Army's Northern Front in 1916–1917.

Selected to attend the Red Army Military Academy at the concluding phase of the Civil War, Cherepanov was one of five volunteers selected from the cadets of the 1923 graduating class to serve as military advisers in China following Foreign Affairs Commissar Joffe's signing of a friendly treaty with China's Kuomintang leader Sun Yat-sen in January 1923, and arrived in Peking on 21 June.

Cherepanov returned to the Soviet Union in 1927, following Sun's death in 1925 and subsequent breakdown in Sino-Soviet relations with the Kuomintang's new leader, Chiang Kai-shek.

With relations between Chiang and the Soviet Union dramatically improved due to the attack on China by Japanese forces in the Second Sino-Japanese War, Cherepanov returned to China as chief military adviser to Chiang's government in Nanking from August 1938 to September 1939 and helped organize the 1938 defense of Wuhan – although the city fell to the combined might of the Japanese troops, planes, and ships.

[2] Assigned to the Red Army's General Staff Academy as a senior instructor after returning from China, Cherepanov was next named Chief Inspector for the Northwestern Direction following the June 1941 German invasion of the Soviet Union in July 1941.