On 6 December 1919, at a military meeting in Nova Chortoria, it was finally decided to carry out a Winter Campaign by units of the UPR and the rear of the Volunteer Army.

The First World War saw tremendous upheaval in Ukraine, and in the short period between the spring of 1917 and late of 1919, three governments had taken shape in the capital, Kyiv.

Originally the main theater of war was the Yelizavhrad Oblast, but as the Bolshevik-Denikin front moved south, so did the campaign.

The main battles of the First Winter Campaign took place at Lypovets, Zhashkiv, Uman, Kaniv, Cherkasy, Smila, Zolotonosha, Olviopol, Holovanivsk, Haisyn, Voznesensk, Ananiv, and Balta.

All returning Winter Campaign participants were awarded the Order of the Iron Cross of the Ukrainian People's Republic.