He went into the field with his regiment in World War I and was wounded in the First Battle of the Marne, falling into French captivity and later internment in Switzerland.

He was promoted to Generalmajor on 1 April 1938 and on 10 November 1938, he was named Oberquartiermeister IV in the General Staff of the Army, placing him in overall charge of military intelligence.

[3] Tippelskirch remained on the General Staff in the early stages of World War II.

[3] As part of Army Group North, the division prevented the breakthrough of a Soviet corps on the river Pola and then went on to counterattack.

In early 1942, the 30th Infantry Division was encircled in the Demyansk Pocket, and Tippelskirch was ordered to be flown out.

On 11 September 1942, he was assigned as the liaison officer of the Italian 8th Army near the Don river.

He retained this position until 4 June 1944, when he had to assume temporary command of the 4th Army from General Gotthard Heinrici.

[4] On 30 July he received the Knight's Cross with Oak Leaves for his achievements in the fighting at Mogilev.

From 29 October to 22 November 1944, he replaced the ailing Otto von Knobelsdorff as the commander of the 1st Army in Lorraine.

[4] On 6 December of the same year, for the duration of the absence of Joachim Lemelsen, he was tasked with the command of the 14th Army during the Italian campaign.

On 29 April however, General Gotthard Heinrici now the commander of Army Group Vistula was dismissed, and Tippelskirch was ordered by Field Marshal Wilhelm Keitel to temporarily take over command of the army group.