| Conflict: | Siege of Kyiv |
| Partof: | Russo-Polish War (1654-1667) |
| Date: | 23-24 August 1658 |
| Place: | Kyiv, Russian Tsardom (modern Ukraine) |
| Result: | Russian victory |
| Combatant1: | Cossack Hetmanate Crimean Khanate |
| Combatant2: | Russian Tsardom |
| Commander1: | Vasili Vyhovsky |
| Commander2: | Vasily Sheremetev Yury Baryatinsky |
| Strength1: | 21,500 to 100,000 |
| Strength2: | 6,075 |
| Casualties1: | 15,000 casualties, 47 banners 9 or 20 cannons |
| Casualties2: | 21 killed, 109 wounded |
| Territory: | Ivan Vyhovsky's plans to capture Kyiv fails |
Siege of Kyiv or Defense of Kyiv was a siege of Kyiv by troops led by Daniil Vyhovsky, whose garrison was commanded by the Russian Commander Vasily Sheremetev. As a result of the battle, Russian troops completely defeated the Cossack regiments and successfully defended Kyiv.
With the death of Bohdan Khmelnytsky, Ivan Vyhovsky became the new hetman of Ukraine. He hoped to build an independent Cossack state, balancing between the Polish-Lithuanian Commonwealth and the Russian Tsardom. The promises of the Polish king John Casimir to make any concessions to the Cossack hetman attracted Vyhovsky and he in turn betrayed Moscow and went over to the side of the Polish-Lithuanian Commonwealth.Vigovskiy also renewed the “brotherly union of Cossacks and Tatars” and secured the support of the talented Crimean commander Karach-Bey.
Already on August 5, Vigovskiy openly declared that he would soon send army to Kyiv.
There was a garrison of 6,075 in Kiev, and it was besieged by a much larger army. Sheremetyev himself wrote that he was probably besieged by an army of 100,000, which included 40,000 Cossacks and 60,000 Tatars. Modern historiography has estimated the number of besiegers at 21,500
On August 16, soldiers sent into the forest ran to Kyiv and reported to Sheremetev that they had been attacked by Cossacks. The colonel sent mounted patrols forward and they confirmed that Cossack regiments were moving from the south to Kyiv. The number of troops near Kiev gradually increased and by evening Vyhovsky himself arrived with the Cossacks and Tatars.
August 23 Daniil began the assault on the city without the hetman's order. Russian troops repelled the Cossacks' attacks and even made a sortie from the golden gate, the Russians started fighting. At the same time, the city was attacked by the Cossacks of Colonel Yanenko, who swore allegiance and promised to enter the battle on the Russian side, as Sheremetev writes: “all his words were lies”. Sheremetev successfully used artillery and sent his riflemen against the rebels.
The castle hill was taken by storm, and the battle that broke out in the south also ended in success for the Russians. However, this was only the first stage of the battle, on the orders of Daniil, Cossacks dug in to the southeast of the city, opposite the Pechersk gates.
At this time, Prince Baratinsky's detachment attacked the main forces of the Cossacks near Vasilkov and they fled, many people died, 47 banners and several cannons