Uprising of Bolotnikov False Dmitry II: Polish–Russian War: In the Battle of Zaraisk, during the Time of Troubles, on April 9, 1608, Colonel Alexander Lisovsky in service of False Dmitry II, defeated the army of Tsar Vasily IV under Zahariya Lyapunov and Ivan Khovansky.

Zaraysk was occupied without a fight by Lisovsky detachments (1,500 Cossacks: "Lithuanian people and Russian thieves"), as the city Cossacks surrendered the city and swore to the Pretender.

[1] An army from Ryazan land came out to suppress the insurrection, to which 250 elite Arzamas warriors joined.

The government army carelessly besieged the fort (with no guards appointed), and the sudden sally of Lisovsky's men from the Zaraisk Kremlin scattered them with little resistance.

However, the detachment of Lisovsky, heavily burdened by the convoy, was defeated by the Tsar's army at Medvezhiy Brod.