St Cyprian's was founded in 1899 by Lewis Vaughan Wilkes and his wife Cicely Comyn, a newly married couple in their twenties.

The school ran with the prevailing ethos of Muscular Christianity which had typified private education since the time of Thomas Arnold of Rugby, and placed much emphasis on developing self-reliance and integrity ("Character").

The school submitted itself annually to an independent academic assessment, conducted by Sir Charles Grant Robertson fellow of All Souls College, Oxford.

The high success rate in achieving scholarships to leading public schools including Eton and Harrow attracted ambitious parents.

The first was the proximity to South Downs, which was fully exploited to give opportunities to the boys for running wild, studying natural history, walking, picnics, riding and even golf on the adjacent links.

In addition to Mrs Wilkes, a major influence was the second master R. L. Sillar, who joined the school staff soon after it opened and stayed for 30 years.

With his interest in natural history, his skill at shooting, his art teaching and his magic lantern shows he broadened the curriculum considerably and is revered in Old Boy's accounts.

Connolly questioned the practice of British parents sending young children to boarding preparatory schools but concluded "Yet St [Cyprian's] where I now went was a well run and vigorous example which did me a world of good.

His friend, George Orwell, disagreed and wrote disparagingly and bitterly of the school in the quasi-autobiographical essay Such, Such Were the Joys, first published in the Partisan Review (Sept.- Oct. 1952).

[14] The thrust of Orwell's criticism was directed at the system of boarding school education that sent children away from their homes when they were no more than 7 or 8 years old, and at the unreflective elitism and classism of Britain before the First World War.