At the start of the First World War he enlisted in the British Army and as a result did not play many matches during the 1914–15 season, but he was given special leave to join Chelsea at Old Trafford for the Cup Final when Bob Thomson was injured. However Thomson recovered and Woodward refused to play and deny Thomson his chance to play in an FA Cup final as Woodward had not played in any of Chelsea's matches in their run to the final.