Russian Civil War
South Russia (1919)

The Cossacks had been unable to organise and capitalise on their successes at the end of 1918. By 1919 they had begun to run short of supplies. Consequently, when the Soviet Russian counteroffensive began in January 1919 under the Bolshevik commander Antonov-Ovseenko, the Cossack forces rapidly fell apart. The Red Army captured Kiev on 3 February 1919.

Denikin's military strength continued to grow in 1919, with significant munitions supplied by the British. In January, Denikin's Armed Forces of South Russia (AFSR) completed the elimination of Red forces in the northern Caucasus and moved north, in an effort to protect the Don district.

On 18 December 1918, French forces landed in Odessa and Crimea, but evacuated Odessa on 6 April 1919, and the Crimea by the end of the month. According to Chamberlin, "France gave far less practical aid to the Whites than did England; its sole independent venture in intervention, at Odessa, ended in a complete fiasco."

Denikin then reorganized the Armed Forces of South Russia under the leadership of Vladimir May-Mayevsky, Vladimir Sidorin, and Pyotr Wrangel. On 22 May, Wrangel's Caucasian army defeated the 10th Army (RSFSR) in the battle for Velikoknyazheskaya, and then captured Tsaritsyn on 1 July. Sidorin advanced north toward Voronezh, increasing his army's strength in the process. On 25 June, May–Mayevsky captured Kharkov, and then Ekaterinoslav on 30 June, which forced the Reds to abandon Crimea. On 3 July, Denikin issued his Moscow directive, in which his armies would converge on Moscow.

Although Britain had withdrawn its own troops from the theatre, it continued to give significant military aid (money, weapons, food, ammunition and some military advisers) to the White Armies during 1919. Major Ewen Cameron Bruce of the British Army had volunteered to command a British tank mission assisting the White Army. He was awarded the Distinguished Service Order for his bravery during the June 1919 Battle of Tsaritsyn for single-handedly storming and capturing the fortified city of Tsaritsyn, under heavy shell fire in a single tank, which led to the capture of over 40,000 prisoners. The fall of Tsaritsyn is viewed "as one of the key battles of the Russian Civil War" and greatly helped the White Russian cause. The notable historian Sir Basil Henry Liddell Hart comments that Bruce's tank action during the battle is to be seen as "one of the most remarkable feats in the whole history of the Tank Corps".

On 14 August, the Bolsheviks launched their Southern Front counteroffensive. After six weeks of heavy fighting the counteroffensive failed, and Denikin was able to capture more territory. By November, White Forces had reached the Zbruch, the Ukrainian-Polish border.

Denikin's forces constituted a real threat and for a time threatened to reach Moscow. The Red Army, stretched thin by fighting on all fronts, was forced out of Kiev on 30 August. Kursk and Orel were taken, on 20 September and 14 October, respectively. The latter, only 205 miles (330 km) from Moscow, was the closest the AFSR would come to its target. The Cossack Don Army under the command of General Vladimir Sidorin continued north towards Voronezh, but Semyon Budyonny 's cavalrymen defeated them there on 24 October. That allowed the Red Army to cross the Don River, threatening to split the Don and Volunteer Armies. Fierce fighting took place at the key rail junction of Kastornoye, which was taken on 15 November. Kursk was retaken two days later.

Kenez states, "In October Denikin ruled more than forty million people and controlled the economically most valuable parts of the Russian Empire." Yet, "The White armies, which had fought victoriously during the summer and early fall, fell back in disorder in November and December." Denikin's front line was overstretched, while his reserves dealt with Makhno's anarchists in the rear. Between September and October, the Reds mobilized one hundred thousand new soldiers and adopted the Trotsky- Vatsetis strategy with the Ninth and Tenth armies forming V. I. Shorin's Southeastern Front between Tsaritsyn and Bobrov, while the Eighth, Twelfth, Thirteenth, and Fourteenth armies formed A.I. Egorov 's Southern Front between Zhitomir and Bobrov. Sergey Kamenev was in overall command of the two fronts. On Denikin's left was Abram Dragomirov, while in his center was Vladimir May-Mayevsky 's Volunteer Army, Vladimir Sidorin 's Don Cossacks were further east, with Pyotr Wrangel 's Caucasian army at Tsaritsyn, and an additional was in the Northern Caucasus attempting to capture Astrakhan. On 20 October, May–Mayevsky was forced to evacuate Orel during the Orel-Kursk operation. On 24 October, Semyon Budyonny captured Voronezh, and Kursk on 15 November, during the Voronezh-Kastornoye operation (1919). On 6 January, the Reds reached the Black Sea at Mariupol and Taganrog, and on 9 January, they reached Rostov. According to Kenez, "The Whites had now lost all the territories which they had captured in 1919, and held approximately the same area in which they had started two years before."
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