Following the outbreak of the Second World War in 1939, Woodward joined the Second Australian Imperial Force as Deputy Assistant Quartermaster-General for the 6th Division, and left for the Middle East in April 1940. In the Middle East he gained distinction during the North Africa Campaign from December 1940 to January 1941 and was invested as an Officer of the Order of the British Empire on 8 July 1941. He served in the Greece Campaign from March to April 1941 as a lieutenant colonel on General Sir Thomas Blamey's staff and later served in the I Corps in the Syrian campaign. In May 1942 he was posted to the 9th Division. He fought in both the First and Second Battles of El Alamein and was awarded the Distinguished Service Order on 11 February 1943. He was twice mentioned in despatches for his work in the Middle East.