Grand Prince Ivan III of Russia pursued expansionist policies, which strained Moscow's relations with Livonia.

In 1492, Moscow built Ivangorod Fortress opposite of Narva and two years later closed down the Hanseatic office in Novgorod.

The armies met on 27 August 1501 on the Siritsa River, 10 km south from Izborsk, on the western approaches to Pskov.

In the battle, the smaller Livonian army defeated the Muscovite army (drawn from the cities of Moscow, Novgorod, and Tver, as well as from Pskov – which was not formally part of Muscovy until 1510) in large part due to the Order's formidable artillery park and the Russians' significant shortage of guns of any kind.

[5] The defeat prompted Moscow to modernize its army by creating standing infantry units armed with arquebus.