The siege began at the early stage of the uprising in January of 1668, when the Cossacks of
Chernihiv regiment led by colonel
Ivan Samoylovych besieged the city as was reported by
Andrei Tolstoy to
Moscow. Most of the city was captured by Cossacks, while the 500-strong garrison led by Andrey Tolstoy was besieged by them in the Upper small town of Chernihiv. On 16 of February,
Ivan Briukhovetsky sent a message to Tolstoy where demanded him to surrender, abandon the cannons and light weapons and retreat to Russia, however he refused. The defenders were conducting raids to the nearby villages. During these raids, the Russians managed to inflict heavy casualties on the besiegers, capture Hetman's flag and some Cossacks. Following the unsuccessful invasion of Russia and
defeat at Sevsk, Doroshenko's Cossacks and Tatars retreated from the Left Bank, which allowed the Russian army to launch a major campaign into Ukraine in September of 1668. On 17 September,
Romodanovsky approached Chernihiv. Demian Mnohohrishny asked help from
Doroshenko but did not receive ot due to Doroshenko's ongoing confrontation with Sukhoviy. On 19–20 September, Romodanovsky launched an assault on 19–20 September which led to firstly New and then Old towns of Chernihiv being recaptured by the Russians and the siege being lifted. Mnohohrishny meanwhile had set off to confront the Russian army but was defeated
at Sedniv on 22 September. Remaining Cossack forces led by Samoylovych were besieged by Romodanovsky in Tretyak district of Chernihiv, which was not assaulted by Romodanovsky, who believed that Samoylovych would soon surrender himself. Romodanovsky however met a strong resistance there which forced him to retreat to
Putyvl on 5 October. ==Aftermath==