After initial successes, in which the city of Oryol at only 360 kilometres (220 mi) from Moscow was taken, Denikin's overextended Army was decisively defeated in a series of battles in October and November 1919.

In mid-1919, the situation on the Southern Front, which in the first months of the year was much better for the Reds, changed in favor of the Armed Forces of South Russia commanded by Anton Denikin.

At the beginning of May, Nykyfor Hryhoriv, who had led the Ukrainian Front of the Red Army in an operation to capture Kherson Governorate from the Allies, revolted against his Bolshevik commanders.

[2] In the northern part of the Don region, Cossacks led an uprising against the local Bolshevik authorities, in response to their repressive policy and persecution of the Orthodox Church.

[1] In June, the White troops under the command of Vladimir Sidorin managed to join the Cossack insurgents and oust the Bolsheviks from the entire Don region.

[4] Finally, in the last days of the same month, the Kuban Cossacks under the command of Pyotr Wrangel, using tanks supplied by the British, captured the strategic southern city of Tsaritsyn.

[7] For this reason Denikin ignored Wrangel's suggestions to postpone a major offensive on Moscow, allow troops to rest, and focus temporarily on defense along the Ekaterinoslav-Tsaritsyn line and only launch an attack [pl] against Astrakhan.

[11] According to Evan Mawdsley, Denikin's Ukrainian offensive was a strategic mistake, as the forces that led it, consequently, could not engage in combat on the key central section of the front, and its line was stretched too thin.

[13] Shorin's group attacked Wrangel's Caucasian Army, which left Tsaritsyn north and was approaching Saratov, but its march was halted due to lack of food and supplies.

[14] Wrangel had to withdraw from Kamyshin and take up a defensive position in Tsaritsyn, where he successfully defended himself; after six weeks of fighting, Shorin's group lost the ability to engage in any offensive actions,[13] especially after it was attacked by cavalry under the command of Konstantin Mamontov.

[14] The Mamontov raid [pl], exploiting the gap between the 8th and 9th Armies, was not included in the original plan of the march to Moscow and may have been undertaken without the consent of Denikin.

[24] On 27 September, impressed by the successes of the Whites, the Southeastern Front was formed from the 9th and 10th Armies, operating on the section from Tsaritsyn to Bobrov under the command of Shorin.

Denikin had practically no reserves, because those troops that were not involved in the march to Moscow were facing engagements with Nestor Makhno's Revolutionary Insurgent Army, which had captured most of eastern Ukraine and were approaching the White headquarters of Taganrog, while a separate group of 3-5 thousand soldiers led the battle for the Red-held Astrakhan.