Two weeks after the death of his great friend, Reggy Secretan, Gerald Henry Greenfield was also killed at Passchendaele. He came from Nottinghamshire and arrived in Sidney House in September 1910. In the Summer Term of 1914, took over as Head of House when Secretan left. He was a School Prefect, played for the XV, described as “an excellent tackler and a good scrummager” and was a sergeant in the OTC. He was a debater, taking part in the debate about whether the pen or the sword is the mightier, coming down firmly in favour of the latter.
Leaving Oundle in the summer of 1915, at the age of 18, he became senior sergeant at the Royal Military Academy, Woolwich. In August 1916, he was gazetted to the Royal Field Artillery and went to the front the next month. On 15th August 1917, he was hit by a sniper while acting as Forward Observation Officer near Zillebeke and died two days later in the Canadian Casualty Clearing Station. He was buried in Lyssenhoek Military Cemetery.
An officer wrote: “He was always so cheerful and absolutely fearless at all times, and a general favourite, not only in his battery but in the whole brigade. We shall miss him sadly – always.”
On his gravestone, his widowed mother, Mary inscribed the words: “Into Thy Hands O Lord”.
His younger brother Charles, also a Sidney boy, joined the Northumberland Fusiliers and became a prisoner of war. In June 1918, he sent his housemaster, Mr Nightingale a postcard from his place of incarceration, showing himself and several other prisoners performing in a play and not looking too badly off, for being in the hands of the ‘beastly Hun’.