The first prince of Pskov was Vladimir the Great's youngest son Sudislav. Once imprisoned by his brother Yaroslav, he was not released until the latter's death several decades later. In the 12th and 13th centuries, the town adhered politically to the Novgorod Republic. In 1241, it was taken by the Teutonic Knights, but Alexander Nevsky recaptured it several months later during a legendary campaign dramatized in Sergei Eisenstein's 1938 movie Alexander Nevsky.

In order to secure their independence from the knights, the Pskovians elected a Lithuanian prince, named Daumantas, a Roman Catholic converted to Orthodox faith and known in Russia as Dovmont, as their military leader and prince in 1266. Having fortified the town, Daumantas routed the Teutonic Knights at Rakvere and overran much of Estonia. His remains and sword are preserved in the local kremlin, and the core of the citadel, erected by him, still bears the name of "Dovmont's town".