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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.

Annual report for the year 1974-1975, including the school numbers, staff changes, academic, faculty reports, chapel, library, drama, C.C.F., Scouts, DofE, Health, School council, Old Oakhamians, Oakham School Nursery Group, The International club, Accomodation, General. With an appendix: job description for public relations co-ordinator and conference organiser

Annual report for the year 1973-1974, including the school numbers, staff changes, academic, faculty reports, chapel, library, C.C.F., Scouts, DofE, Health, accomodation, Old Oakhamians, Nursery School, General.

Annual report for the year 1970-1971, including the school numbers, staff changes, academic, faculty reports, chapel, library, drama, C.C.F., Scouts, DofE, Health, accomodation, School Shop, Old Oakhamians, Second development Campaign, School House, General, the Chaplaincy