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This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

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 file relates to the Headmaster's Annual report to the Trustees, from the 1950s to 1980s. The reports cover all aspects of School, academic, examination results, extra-curricular activities, Estates and Maintenance, staff and individual faculty report, vision for the future of the School. All reports are private and confidential.

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.