Cnezatul Moscovei
The area of the district in the Middle Ages was interchangeably under control of the Novgorod Republic, Principality of Smolensk, and the Lithuania. In 1335, the war between Lithuania and the Grand Duchy of Moscow started, and in the beginning of the 15th century the area was transferred to the Grand Duchy of Moscow. The Dubna Volost, currently a part of the town of Andreapol, was mentioned in the chronicles in 1489. After several wars between Moscow and Lithuania, during which the area was transferred to Lithuania and back, it was in 1508 again included to the Grand Duchy of Moscow.