Kutepov graduated from Junker Infantry School in St. Petersburg in 1904. As a young infantry officer, he fought in the Russo-Japanese War, where he was severely wounded in action and decorated for valor. In 1906, he was transferred to the Preobrazhensky Regiment, an elite guards regiment. During World War I, he received several decorations for bravery and was again severely wounded in action. During the course of the war, he rose from company, to battalion to commander of the Preobrazhensky Regiment. As such, he became the last commander of this historic regiment.
After the October Revolution, Kutepov joined the anti-Bolshevik Volunteer Army (part of the White Movement) at the very outset of the Russian Civil War. At the start of the Ice March in early 1918, Kutepov was a company commander of an officer's regiment. (In the beginning of the Russian Civil War the small Volunteer Army had a surplus of officers, which meant that many of them had to serve as common soldiers. These formations soon became the crack units of the White Army.) After the death in battle of Colonel Nezhentsev, Kutepov took over the command of the Kornilov Shock Regiment, and after the death of the commander of the 1st Infantry Division, he became its commander. When the Whites captured Novorossiysk in August 1918, Kutepov was appointed Governor General of the Black Sea region.
Starting in January 1919, 36-year-old Lieutenant General Kutepov became the commander of the I Army Corps of the White Army. Throughout his career, Kutepov had a reputation for being a decisive, direct and no-nonsense military leader. During the chaotic times of the Russian Civil War, order was usually rapidly restored after Kutepov's arrival. He accomplished this, however, by means of the swift and ruthless application of the death penalty on suspected looters and pogrom perpetrators.
After the White Army's final defeat in the Crimean Peninsula, Kutepov and the remnants of his corps evacuated to Gallipoli in November 1920. Despite very unfavourable and demoralizing circumstances, the troops in Gallipoli regained their morale and kept their military coherence thanks to Kutepov's leadership. In the beginning of the Gallipoli period, Kutepov was disliked by many of the troops because of his disciplinary measures, but by the end, he was warmly regarded by most of them. When the Gallipoli camp was disbanded, Kutepov moved to Bulgaria in late 1921. Two years later he was expelled from the country during the upheavals of the Aleksandar Stamboliyski era. Kutepov and his wife settled in Paris. After General Pyotr Nikolayevich Wrangel's death in 1928, he became the leader of the Russian All-Military Union and continued its anti-Soviet activities.
On 26 January 1930, Kutepov was kidnapped in Paris by OGPU agents. According to Pavel Sudoplatov,
"This job in 1930 was done by Yakov Serebryansky, assisted by his wife and an agent in the French police. Dressed in French police uniforms, they stopped Kutepov on the street on the pretext of questioning him and put him in a car. Kutepov resisted the kidnapping, and during the struggle, he had a heart attack and died, Serebryansky told me. They buried Kutepov near the home of one of our agents near the outskirts of Paris."
Kutepov was believed by French police of having been smuggled to the Soviet Union. Former White Army general Nikolai Skoblin, an Inner Line member, was suspected of being an accomplice in his kidnapping. Walter Laqueur alleges, "Skoblin had nothing to do with this affair, because he was recruited only after Kutyopov's disappearance." KGB General Sudoplatov confirms this allegation in his own memoirs.