During the initial invasion of the Soviet Union, 5th SS Wiking was assigned to Army Group South, where they advanced through modern-day Ukraine. Wiking assisted in the capture of Uman and Ukraine and continued East until creating a defense along the Mius River.

During the initial invasion of the Soviet Union, 5th SS Wiking was assigned to Army Group South, where they advanced through modern-day Ukraine. Wiking assisted in the capture of Uman and Ukraine and continued East until creating a defense along the Mius River.

During the Winter of 1941-42, the Soviets launched a counter-offensive in the hopes to secure Izium and push the Germans away from Moscow. The Soviets regained territory in the North and drove the Germans away from Moscow, but made little progress against Army Group South. The offense collectively failed, with the Germans launching a counter-offensive in the Second Battle of Kharkov in mid May.

Wiking was supplied with reenforcements in preperation for the offensive, including foreign volunteers and tanks. The battle was an overwhelming success for the Germans, with Wiking being one of the first SS divisions to be awarded a panzer battalion. In the Summer, Wiking and Army Group South continued their advance to Rostov and the Caucasus to capture the Maikop oil fields. In the Fall, Wiking assisted in the capture of the city of Grozny, but ultimately failed in their objective. Due to their success in battle, Wiking was awarded the status of Panzergrenadier Division.

In the Winter of 1942-43, the Soviets succeeded in encircling and destroying the German 6th Army, which resulted in Wiking and Army Group South to retreat and attempt to relieve Army Group North. After the relief failed, Wiking was assigned for a second attempt to retake Stalingrad, but was instead tasked with covering the retreat of the First Panzer Army back through Rostov.

Early 1943, Wiking took defensive positions in Ukraine near Kharkov. In the summer, the Soviets regained Kursk and continuted with addition offensives in Kursk and Kharkov. Wiking participated in securing the Mius River, but was forced to retreat to Dnieper in August after the Sovets captured Kharkov.

In the retreat West during the Winter of 1943-44, the Soviets encircled a large number of German divisions, including Wiking, in what was known as the Cherkassy Pocket. During the break-out, Wiking was the only division that was equipped well enough to protect the retreat against aggressive Soviet offensives, and covered the advance South. Before breaking out of the Pocket, the Germans faced a large river with no bridge or support to cross. The troops were forced to surrender nearly all of their equipment, vehicles, and heavy weapons to cross. The soldiers swam across the icy water and found their way out of the Pocket.

In early 1944, Wiking was refitted and reorganized after the Cherkassy Pocket and sent to Kovel to defend against Soviet advances. While advancing into the city, part of the division was surrounded by Soviet forces and unable to escape. The remainder of Wiking's 5th Panzer division and 8th/Pz.Rgt.5 broke through Kovel in March and were able to resupply and reinforce the surrounded troops. Wiking held their defenses of the city until April, when they were ordered West to defend parts of Western Ukraine.

Wiking continued to retreat through Hungary, where they fought in Operation Konrad I, II, and III to relieve forces in Budapest. Wiking was never able to break through to the city and suffered heavy casualites. By February they were ordered West to Lake Balaton to conduct an offensive. The attack was successful at first, however, muddy terrain and strong Soviet defenses brought the attack to a halt. In mid March the Soviets launched am overwhelming counter offensive, breaking the German lines and forcing Wiking to retreat into Czechoslovakia. Soldiers who were lucky in the retreat surrendered to British forces in Vienna on May 8th, while some were captured or surrendered to the Soviets while moving through Bohemia.