At 24, Alexander becomes a second lieutenant. In 1805, Chechenskiy was transferred to the Grodno hussar regiment, where he commanded a half-squadron. In 1805–1807, he took part in battles with Napoleon's troops near Myshenitsy, Gutshtadt, Ackendorf, as well as in driving the enemy across the Posarzha River. The courage of Chechenskiy under Gutshtadt was marked with a golden weapon. For bravery in the battle of Preussisch-Eylau, Alexander was awarded the Order of St. Vladimir, IV degree with a bow.