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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.

Items related to Walter Lee Sargant's book "Oakham through the centuries".

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

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 Remembrance services held in the Chapel or other churches in Oakham.

This sub-series contains photographs of various Duke of Edinburgh expeditions, since the 1980s.

This sub-series focuses on photographs of boys, living in Junior House/Chapmans since its inception. The bulk of the collection gathers photographs from the 1950s to 1980s.

This sub-series focuses on photographs of boys in School House since the 1940s.

This sub-series focuses on photographs of the Junior Boarding boys of Sargants House. The collection is complete from 1966 to 2010, missing only the years 1970 and 2009.

This sub-series focuses on photographs of girls in Orchard Close and Buchanans House, mostly in the 1990s and early 2000s. It also contains photographs of the Sixth Form cohort.