Headmaster
In 1940, after eight years as Master of the Lower School, Phillips was appointed as the sixth Headmaster of Sydney Grammar School. On his appointment he was 61 and the war years were difficult for the school. Sir Victor Windeyer said of his term of office: "The Headmaster wisely and modestly considered that his task was to preserve the heritage of the past so far as he could, so that on it his successor might build. He saw the need for changes and developments in the School to meet the challenge of change outside; but these, he felt should be begun by those who would carry on." He had been an inspirational teacher and had substantially improved the cultural life of the school even for a student like Max Dupain who was not scholastically inclined; "Thanks to my English sixth form master, Sandy Phillips, I learned to love Shakespeare".
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