The battle began when Makhno, Shchus, and a group of anarchist supporters ambushed Austrian and Ukrainian detachments stationed in Dibrivka.

[5] The anarchists were forced to retreat to Russia, where they regrouped in Taganrog and planned to launch a war of independence against the occupying powers.

[7] The insurgent leader Nestor Makhno clandestinely returned to his hometown of Huliaipole, where he held secret meetings with other anarchists, with whom he made plans to ignite an insurrection against the occupation forces.

The anarchists then withdrew north to Pokrovske, where they launched another surprise attack against the Austrians and briefly captured the town from the occupying powers.

They were swiftly joined by Vasyl Kurylenko in Berdiansk and Petro Petrenko in Hryshyne, which greatly expanded the insurgents' sphere of influence to cover most of Katerynoslav and Northern Tavria.

[26] Supported by seizures from the local landowners and with increasing disaffection among the ranks of the occupying forces, the insurrection spread throughout southern and eastern Ukraine, with Tsarekostyantynivka and Dibrivka both briefly falling under anarchist occupation.

[31] On 23 January 1919, Dibrivka played host to the First Regional Congress of Peasants, Workers and Insurgents, which discussed how to strengthen the frontlines against the forces of the Ukrainian nationalists and the White movement.

[32] Soon after, the Makhnovshchina made a pact with the newly established Ukrainian Soviet Socialist Republic and the insurgents were integrated into the Red Army.