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This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

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 series relates to wages and salary paid to teaching and support staff, including a salary book and pay sheets.

This series focuses on the Day boys of Clipsham, founded in 1997. The main items are house photographs and handbooks.