He first saw active service in the First World War, which began in August 1914, on the Western Front. Over the course of the war he was mentioned in despatches twice, wounded once and received the Military Cross and two Bars for gallantry and leadership.[4] The citation for his MC reads:
For conspicuous gallantry and resource on the afternoon of 26th September, 1915. Some new troops holding a corner of "Fosse 8" were shaken by heavy shell fire, and, believing that the enemy were holding the Slag Heap in their rear, were on the point of retiring, when Lieutenant Woolner rallied them, and, collecting two sections of his own company, charged to the top of the Slag Heap and restored' confidence.
A retirement at this point would have been very serious.
From October 1917 to July 1918 Woolner, promoted on 4 December 1914 to lieutenant,[5] was Commanding Officer (CO) of the 64th Field Company, Royal Engineers.[1][2]
Between the wars, Woolner served with the Royal Engineers in Gold Coast, Woolwich, India and Chatham. He attended the Staff College, Camberley from 1927 to 1928.[1]