Personal: Born at St Peter's Vicarage, Bethnal Green, London on 14 May 1892, son of the Rev George Herbert Woolley (who had been working in the East End of London for over twenty-five years) and of Sarah Woolley (nee Cathcart). He was educated at St John's Leatherhead and at Queen's College, Oxford and joined the Army on 4 August 1914 as a Second Lieutenant in the 5th Battn the Essex Regiment. When the Essex Territorial Brigade was split up in Sept 1914, he was transferred to the 9th Battn The London Regiment (Queen Victoria's Rifles) and went out to France with them in November 1914. Sir Arthur Conan Doyle wrote in "The British Campaign in France and Flanders in 1915" (page 40): "Tuesday, 20 April, was another day of furious shell fire. A single shell upon that morning blew in a parapet and buried Lieut Watson with twenty men of the Surreys. The Queen Victoria's under Colonel Shipley, upheld the rising reputation of the Territorial troops by their admirable steadiness. Maj Lees, Lieut Summerhayes, and many others died an heroic death; but there was no flinching from that trench, which was so often a grave. As already explained, there was only one trench and room for a very limited number of men on the actual crest, while the rest were kept just behind the curve, so as to avoid a second Spion Kop. At one time upon this eventful day a handful of London Territorials, under a boy officer, Woolley of the Victoria's were the only troops upon the top, but it was in safe keeping none the less."

"Deeds that Thrill the Empire" (page 873) says: "Early in the eventful August of 1914, a young undergraduate of Queen's College, Oxford, the son of a clergyman, and who, but for the outbreak of war, would have been by this time a clergyman himself, joined the 5th Battn Essex Regt., and went with them to Drayton near Norwich, where that unit was to undergo its training under the command of Colonel J.M. Welch. His stay with the 5th Essex was very brief, however, for on 26 August he was transferred to the Queen Victoria's Rifles. This young man was Second Lieut Geoffrey Harold Woolley, who was to have the honour of being the first Territorial officer to win the Victoria Cross. The Queen Victoria's Rifles crossed the Channel in November 1914 and in due course proceeded to take their turn in the trenches with the regular battalions of the 5th Division, to which they were attached, when they came in on occasion for some pretty severe shelling. But they were not employed in attack until the affair at Hill 60 in the following April, which was an experience none of them is ever likely to forget. Hill 60 - hill by the way, only by courtesy, since it is, in point of fact, merely an earth-heap from the cutting of the Ypres-Lille railway - lies a little to the west of Klein Zillebeke and just east of the hamlet of Zwartleben, the scene of the famous charge of our Household Cavalry on the night of 6 November 1914. Its importance was that it afforded an artillery position from which the whole German front in the neighbourhood of Chateau Hollebeke could be commanded. At seven o'clock in the evening of 17 April, the British exploded seven mines on the hill, which played havoc with the defences, blowing up a trench line and 150 men, after which, under cover of heavy artillery fire, the position was stormed by the 1st West Kents and the 2nd King's Own Scottish Borderers, who entrenched thenselves in the shell craters and brought up machine guns. During the night several of the enemy's counter-attacks were repulsed with heavy loss, and fierce hand-to-hand fighting took place; but in the early morning the Germans succeeded in forcing back the troops holding the right of the hill to the reverse slope, where, however, they hung on throughout the day.