Administratively, Pskov Oblast is divided into two cities and towns of oblast significance and twenty-four districts.
In terms of the population, the biggest administrative districts are Pskovsky District (34,323 in 2010) and Ostrovsky District (31,096), the smallest one is Usvyatsky District (5,598).
In terms of the area, the biggest administrative district is Bezhanitsky District (3,535 square kilometres (1,365 sq mi)), the smallest one is Pushkinogorsky District (1,059 square kilometres (409 sq mi)).
The municipal divisions of Pskov Oblast are identical with its administrative divisions. All of the administrative districts of Pskov Oblast are municipally incorporated as municipal districts, and the cities of oblast significance are municipally incorporated as urban okrugs.
Historically, the whole area of the oblast was dependent on the Novgorod Republic and was annexed by the Grand Duchy of Moscow in the 15th and the 16th centuries. The southern part of the oblast was the battleground area and changed hands frequently, before landing in Poland by the end of the 16th century. December 29 [O.S. December 18], 1708 Tsar Peter the Great issued an edict which established seven governorates. The description of the borders of the governorates was not given; instead, their area was defined as a set of towns and the lands adjacent to those towns. The present area of Pskov oblast was a part of Ingermanland Governorate, which was renamed Saint Petersburg Governorate in 1710. The governorates were subdivided into uyezds, and uyezds into volosts. In 1727, a separate Novgorod Governorate was established. It was subdivided into five provinces, and the current area of Novgorod Oblast was split between two of them - Pskov and Velikiye Luki Provinces. In 1772, after the First Partition of Poland, vast areas which formerly belonged to Poland were annexed by Russia, and in order to accommodate them, Pskov Governorate, with the center in Opochka, was established, and Pskov and Velikiye Luki Provinces, with the exception of Gdovsky Uyezd, were transferred to Pskov Governorate. All current area of Pskov Oblast belonged to Pskov Governorate, with the exception of the areas currently belonging to Gdovsky, Plyussky, and Strugo-Krasnensky Districts. These belonged to Saint Petersburg Governorate.Porkhovsky Uyezd belonged to Novgorod Governorate until 1776, and then it was transferred to Pskov Governorate.