Troubetzkoy received home education, since 1806 he was attending lectures in the Moscow University. In 1808 he entered Leib Guards Semyonovsky regiment. As a soldier, he participated in all significant battles of Sixth Coalition campaign in 1812-1814 including battle of Borodino, battle of Maloyaroslavets, Battle of Lützen, battle of Bautzen and battle of Kulm and received many orders. In the battle of Leipzig he was badly wounded. After the war he continued military service and in 1821 he was promoted to Colonel.