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A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

A collection of documents, chiefly photographs, of Wharflands, purchased by the then Headmaster Walter Lee Sargant in 1920. The property was converted into a boys’ boarding house for twenty-six boys, while the Old Stables were used for other school purposes. Extension work began in 1928, adding four new dormitories and a large dining hall. The O.T.C. established its headquarters in the new extension. With the boys now living in the extension, the Housemaster and his family could occupied the old house. The first floor was converted into some classrooms, for the teaching of Science and Maths. In 1960 and 1977, a series of improvement and refurbishment work started and changing rooms were modernised, while new rooms were added.