Woldenga's career started as a captain in the merchant marine. He started his flight training in 1928 and worked as chief pilot for the FVK Warnemünde. He transferred to the newly emerging Luftwaffe, taking command as "Gruppenkommandeur" of the I./Jagdgeschwader 131 (JG 131) — later renamed to I./Jagdgeschwader 1 (JG 1) — on 1 April 1937. With this unit he participated in the invasion of Poland in 1939. He surrender command of the "Gruppe" on 1 February 1940 and was transferred to the "Reichsluftfahrtministerium". He briefly led Jagdgeschwader 27 (JG 27) on the Channel Front from 11 October to 22 October 1940 before he was made "Geschwaderkommodore" of Jagdgeschwader 77 (JG 77). Under this command, JG 77 participated in the Balkans Campaign and invasion of Crete. JG 77 claimed 50 aerial victories. Woldenga received the Knight's Cross of the Iron Cross. He commanded of JG 27 on 21 June 1941 during the invasion of the Soviet Union and claimed 4 aerial victories. He relocated the Geschwaderstab to North Africa in December 1941. He was appointed "Fliegerführer Balkan" on 10 June 1942. His last service position of the war was commander of the "Luftkriegschule" 10 in Fürstenwalde near Berlin. He is credited with three aerial victories of which two were claimed on the Eastern Front.