Between August 5 and 8, fighting took place at the wide approaches to the city of Odessa. Subsequently, the Soviets retreated to the outer defensive ring. This was located 20 to 25 kilometers from the city. Just one day later, the Romanian 1st Armored Division broke through the first line of defense and continued to push toward the second ring. On August 13, the Soviet lines to the east of the city were broken through, thus completely enclosing Odessa from the land side. The Romanian armored troops suffered heavy losses in the process, because they only acted in small groups and separately from or poorly with their own infantry.
After encircling the city, Marshal Antonescu's offensive continued on August 16. On the 17th, Romanian troops captured Odessa's water reserves. Repeated Soviet counterattacks were repulsed in the process. On the night of 18 August, Romanian Navy torpedo boats damaged a Soviet destroyer. The Luftwaffe also repeatedly intervened in the fighting by ground forces, attempting to cut off maritime traffic to and from Odessa and destroying a Soviet armored train on 20 August. On 19 August, the Odessa Defense District was formed, with Rear Admiral Gavrill Zhukov, commander of the Odessa Naval Base, in charge. The following day General Petrov was appointed commander of the 25th Chapaevsk Rifle Division, which together with the 95th Rifle Division (Major General Vorobyev) bore the brunt of the defense.
On August 20, the Axis forces began a new offensive involving 17 divisions and 7 brigades concentrated around the city:
- III Corps, Major General Vasile Atanasiu (2nd, 3rd, 7th and 11th Infantry Divisions)
- I Corps, Major General Teodor Ionescu (1st Guards and 21st Infantry Division)
- IV. Corps, General Constantin Sănătescu (8th and 14th Infantry Division)
- V. Corps, Major General Aurelian Sion (1st, 4th, 13th, and 15th Infantry Divisions).
- XI. Corps, Constantin Constantinescu (6th, 10th and 21st Infantry Division)
- Reserve: 5th Infantry, 1st Frontier Guard and 1st Armoured Divisions, 9th Cavalry Brigade
After a month of prolonged fighting, the Romanians came within 10 to 14 km of Odessa. Between 5 and 24 August, the Romanian 4th Army attacks had already resulted in 27,307 men (5,329 killed, 18,600 wounded and 3,378 missing) in casualties. By 24 August, the Red Army's main defensive line at Kagarlyk had been pushed back toward Karstal. Romanian artillery was able to shell the town's harbor from their positions.
| About 38,000 people of the Red Army, the Ministry of the Interior and civilian life were awarded the medal for the defense of Odessa. |
| Soviet stamp issue from 1965 for the nomination of Odessa as a hero city |
Between August 28 and 30, a Soviet counterattack took place, which drove back the attackers and gave them back the initiative only on the last day. For a time the village of Kubanka was liberated. In the renewed attack by the invaders, Soviet troops were encircled in Vakarzhany and routed by 3 September. An offensive launched on September 12 had to be abandoned just two days later due to a lack of ammunition for the German and Romanian artillery.
Because the attacks under Lieutenant General Ciuperca did not penetrate despite strong superiority, he was replaced by General Iosif Iacobici on September 10. On September 22, the Soviet forces, repeatedly reinforced from the sea, began a counterattack. The Axis forces were pushed back 5 to 8 km and two Romanian battalions were crushed.
After the German breakthrough into the Crimea on 29 September 1941 under General Erich von Manstein and the threat to the Donets Basin as well as Sevastopol, the Soviet High Command decided to evacuate Odessa. From October 1 to 16, 86,000 Red Army personnel were evacuated to protect the Crimean Peninsula, as well as 15,000 inhabitants by the Black Sea Fleet. The Romanian Air Force flew jamming attacks on the evacuation fleet. On October 16, Axis forces entered Odessa.