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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.

Two letters (A and B) to Roger Blackmore, new Chairman of the Holiday Lettings Committee, and to Nigel Webb, member of the Committee, regarding the new company and their new roles.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

The items in this collection are related to Tutoring at Oakham School, either guidelines to staff or resources to use in tutorial with the pupils.

A letter from Graham Smallbone, Headmaster, to R.M.P. regarding the accommodation for the Australian Gap Year students and their role within the school. Two pages numbered A and B.

A letter from the Headmaster Tony Little to Parents regarding a review of the Winter term 1996. Contents: Achievements in Drama, Music and Sports; Parent/Teacher Committee; Matters Academic; Building Development; Staff.

A photograph of Lower School staff, including Joan Shorten, celebrating her 25th anniversary at Oakham School in February 1999.

A letter from the Headmaster Tony Little to Parents regarding a review of the Summer term 2001. Contents: Speech Day; Sporting achievements; Trips; Examinations results; Curriculum and Subject choices; Changes of Staff; Beginning of term dates; Dates further into the future.

A group of photographs (A to P) of Tony Little's leaving do in Stumps in 2002.

A headmaster's annual report for the academic year 1974-1975. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; The School Council; Old Oakhamians; The Oakham School Nursery Group; The International Club; Accommodation; General. Attached is a job description for a Public Relations Co-Ordinator and Conference Organiser (appendix A). Seven pages A to G.