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This series is related to school fees and tuition. Items include reports from the Bursar on increase of fees, balance sheets, and individual pupils' bills.

This series is related to the charity work at Oakham School, including the fund raising and other events organised at school by staff, pupils, houses and the Oakham School Charities Association (OSCA) in aid of various charities and the local community.

This file relates to Jon Wills's time at Oakham School as a pupil and staff.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

A collection of material which focuses on Old Oakhamians who fell in the First World War, containing personal and family items and research.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

This series focuses on Round House pupils and staff since its opening in 1972 as the first purpose-built girls' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.

This series focuses on the Day girls of Gunthorpe, founded in 1997. The main items are house photographs.

This series focuses on Stevens House pupils and staff since its opening in 1989 after the conversion of Deanscroft, a former boys' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.

A collection related to the History of Oakham School since its foundation, including research on Headmasters, Masters and pupils, and articles and books published by Headmasters and teachers.