Novgorod Oblast
Towards the end of the 15th century, Novgorod was defeated by the army of Ivan III, the prince of Moscow. It was included into the Grand Duchy of Moscow. In 1560, Ivan the Terrible, fearing treason, sent his army to sack the city. This event was known as the Massacre of Novgorod. It had terrible consequences for the city, which lost the majority of its population and never recovered.  Additionally, Novgorod was looted by the Swedish army in the beginning of the 17th century, during the Time of Troubles.