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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.

A copy of John Buchanan's book 'Operation Oakham', published by the Sycamore Press in 1984.The book tells the story of Oakham School's independence and the start of co-education. There is a dedication to Edward Leigh, dated from 7 January 1985.