Siege of Odessa ( 1941 ) The Siege of Odessa was part of the Eastern Front area of operations in 1941 , it was primarily conducted by Romanian forces and elements of the German Army ' s ( " Wehrmacht Heer " ) 11th Army ( " 11 . Armee " ) . Due to the heavy resistance of the 9th Independent Army ( initially ) and the rapidly formed Separate Coastal Army , which was formed from the Coastal Group of the 9th Army , and the Black Sea Fleet forces in Odessa , it took the Romanian army 73 days of siege and four attempts to take the city , during which they suffered 93 , 000 casualties , while the Red Army suffered around 41 , 000 casualties . Other claims however , suggest the Red Army suffered 60 , 000 casualties . Prelude . On 27 July 1941 , Hitler sent a letter to General Antonescu in which he requested further cooperation of the Romanian troops beyond the Dniester River , and granted the Romanians administration of the territory between the Dniester and the Bug rivers . Antonescu accepted on 31 July . In fact the Romanian Third Army had already crossed the Dniester on 17 July . Lieutenant - general Nicolae Ciupercă ' s Fourth Army commenced the advance over the river on 3 August . The 5th Corps , comprising the 15th Infantry Division and 1st Cavalry Brigade , forced the crossing between Tighina and Dubăsari . During the night of 5 August , the 1st Armored Division also joined the 5th Corps . On 8 August , the Romanian General Staff issued the Operative Directive No . 31 stipulating that the 4th Army was to defeat the enemy between the Dniester River and the Tiligulskiy Bank and to occupy Odessa from the move . It was thought that the city garrison , which was heavily outnumbered , would surrender quickly . However , Odessa was a heavily fortified position , which , thanks to the superiority of the Soviet Black Sea Fleet , could not actually be completely surrounded . The defense was organized on three lines with trenches , anti - tank ditches , pillboxes and others . The first line was 80 km long and situated some 25 – 30 km from the city . The second and main line of defense was situated 6 – 8 km from the city and was about 30 km long . The third and last line of defense was organized inside the city itself . The forces that initially manned the fortifications were made up of the 25th and 95th Rifle Division s , the 2nd Cavalry Division , the 421st Rifle Division , the 54th Rifle Regiment and an NKVD Regiment . Overall , the Red Army had some 34 , 500 men and 240 artillery pieces in the area . Air support was provided by the 69 IAP , two seaplane squadrons and one bomber squadron . Later , other fighters joined the defenders , as did an Il - 2 squadron . Bombers from Crimea and Nikolaev also participated in the battle . The 4th Army planned a combined maneuver : the 3rd Corps ( 3rd , 7th Infantry and 1st Guard Divisions and the 2nd Tank Regiment ) had to undertake a frontal attack on the Razdelnaya – Odessa direction , while the 5th Corps ( 15th Infantry and 1st Armored Divisions and 1st Cavalry Brigade ) executed a turning maneuver to the north , towards Katargy and Bolschaya Buzhalyk , and then turn southwards . The 3rd Reconnaissance Group of the 3rd Infantry Division advanced towards Razdelnaya and reported that the village was burning and the railway station was occupied by Soviets troops . In the evening , the 1st Armored Division and the 1st Cavalry Brigade encircled Katargy and took 200 Soviet POWs . Battle . On 9 August , the 4th Dorobanti Regiment defeated the Soviet forces in the Bakalovy area , while the 30th Dorobanţi Regiment took hold of the village of Ponyatovka . The 7th Infantry Division occupied the Razdelnaya railroad station and a plateau south of the station , despite heavy Soviet resistance . The following day , in the sector of the 3rd Corps , the bulk of the 7th Infantry Division reached Elssas , while the 1st Guard Division arrived on the alignment Strassburg – Petra Evdokievka . In the sector of the 5th Corps , the 1st Armored Division advanced fast and defeated the Soviet forces at Bolschaya Buzhalyk , breaking through Odessa ' s first line of defense . Until the evening , the Romanian division reached the second line of defense , on the alignment Blagodatnaya – Mal . Adzhalyk . The 1st Cavalry Brigade took Severinovka and joined the 1st Armored Division . At the same time , the 10th Dorobanţi Regiment overran the Soviet forces at Lozovaya . The 4th Army gradually closed the circle around Odessa , but the offensive was temporarily stopped by Antonescu on 13 August to strengthen the line west of the Hadjibey bank . The offensive resumed on 16 August , as Romanian troops attacked along the entire line , capturing Odessa ' s water reservoirs on 17 August . The Soviet forces put up a stubborn resistance , launching repeated counter - attacks , inflicting and taking heavy casualties . The Royal Romanian Air Force actively supported the ground troops , disrupting Soviet naval traffic to and from Odessa , and also destroying an armored train on 20 August . During the night of 18 August , two Romanian torpedo boats ( NMS Viscolul and NMS Vijelia ) attacked and damaged a Soviet destroyer south of Odessa . It was one of the few actions the Romanian Navy undertook to support the siege . By 24 August , despite constant attacks , the Romanians were bogged down in front of the Soviets ' main line of defense . The 4th Army had already suffered 27 , 307 casualties , including 5 , 329 killed in action . Nevertheless , the Soviets were also weakened , and thanks to the capture of Kubanka , Romanian heavy artillery now threatened the port of Odessa . Over the next three days , there was a lull in the fighting . On 28 August , the Romanians resumed their offensive , reinforced by a German assault battalion and ten heavy artillery battalions . The 4th , 11th and 1st Army Corps advanced towards Gnileakovo and Vakarzhany , only to be pushed back in some areas by a strong Soviet counterattack the following day . On 30 August the Romanians retook the initiative , but gained very little ground . The Soviets temporarily retook Kubanka but were driven back by nightfall . Soviet troops in Vakarzhany were encircled and continued to fight until 3 September , when combined German and Romanian infantry successfully stormed the village . On 3 September , General Ciupercă submitted a memoir to by - now Marshal Antonescu , highlighting the poor condition of the front - line divisions , which were exhausted after nearly a month of continuous fighting . He proposed a reorganization of six divisions ( the 3rd , 6th , 7th , 14th , 21st Infantry and Guard Divisions ) , which would be split into 2 corps and supported by 8 heavy artillery battalions . These units would then attack in a single area to break through the Soviet line . The memoir however , was rejected by both Antonescu and Bridagier - General Alexandru Ioaniţiu , the chief of the Romanian General Staff , who argued that an attack in a single direction would leave the rest of the Romanian line too exposed . Marshal Antonescu subsequently issued a new directive calling for attacks between Tatarka and Dalnik , and Gniliavko and Dalnik , to be made by the 11th and 3rd Corps , respectively . Ioaniţiu forwarded a note to Major - General Arthur Hauffe , the chief of the German military mission to Romania , informing him of the situation at Odessa and requesting assistance in the form of aircraft and several pioneer battalions . Although the Royal Romanian Air Force enjoyed some success against the Soviets ground and air forces , it was ill - equipped for anti - shipping raids , and the Soviets were being steadily reinforced and resupplied via the Navy . Meanwhile , the Romanian offensive was halted to wait for reinforcements . A German detachment led by Lieutenant - General René von Courbier and comprising one infantry regiment , one assault pioneer regiment and two artillery regiments arrived . Concurrently , the Soviets also received 15 , 000 men and ammunition . On 9 September , Ciupercă was replaced by Lieutenant - General Iosif Iacobici , who was expressly ordered to follow the General Staff ' s directives without question . The offensive resumed on 12 September , but was again stopped temporarily on September 14 as Romanian and German artillery units were running low on ammunition . Two Vanatori battalions were encircled by Red Army troops near the Hadjibey bank , but were eventually relieved despite Soviet efforts to annihilate them . On the night of 15 September , Soviet troops broke contact with the Romanian 1st Corps and retreated toward the southeast . On 16 September , the 1st Corps took the heights northwest of Gross - Liebenthal . Romanian troops also occupied the area south of the Sukhoy bank . Over 3 , 000 Soviet soldiers were captured , but these losses were replaced by the 157th Rifle Division , with a strength of 12 , 600 troops . Also , 18 Soviet companies were brought in from Novorossiysk . Aftermath . With the advance of Axis forces into the Soviet Union , STAVKA decided to evacuate the defenders of Odessa . On the night of 14 – 15 October 1941 , the Black Sea Fleet evacuated the garrison to Sevastopol where most of the units were later destroyed in the bitter fighting that took place there . The Black Sea Fleet also managed to evacuate 350 , 000 soldiers and civilians . Casualties suffered during the Siege of Odessa were :