By December 1590, Golitsyn has been appointed governor of the " Polk levoy ruki", the "Regiment of the Left Hand" which was the organizational and tactical unit of the Russian army in the 11th-17th centuries. (In the battle, the regiment of the left hand was part of the main forces and accordingly formed the left flank of the battle formation of the army.) He led this regiment in the Russo-Swedish War. By 1591 he served as the first governor in the fortress of Dedilov. From there he was recalled to Moscow in order to strengthen its defense during the invasion of the Crimean army under the leadership of Khan Gaza Girey. After the retreat of the khan from Moscow, Prince Vasily Golitsyn led the right-hand regiment to Tula.