When was the farthest advance of axis power?

Answer 1

The farthest advance of Axis powers were either Germany to France, Germany to Russia, or Italy to Africa.

In early 1942, the Axis powers controlled most of continental Europe (except the Iberian peninsula and Russia east of Stalingrad), North Africa and all former French and Belgian colonies. The Japanese controlled most of China's population, Indochina, Thailand, Indonesia, and most of the Pacific Islands. The Allies began to turn the tide with victories at Midway, Stalingrad, and El-Alamein.

Answer 2

Stalingrad on the Volga river.