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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 file related to Registrar's annual reports, submitted to the Headmaster and Trustees. The file dates from the headmastership of Graham Smallbone.

The Oakhamian Magazine, recording the Spring and Summer terms 1979. Contents: Editorial; School News; Valedictions; Opinion; Excursions and Adventures; Clubs and Societies; Drama; Music; Sport; The School Council.

A prospectus promoting studying at Oakham School in 1902. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

A letter from the Acting Headmaster Michael Stevens to Parents regarding the Quatercentenary Appeal, school trips, the annual Sixth Form Conference, Sports fixtures, and Open Day for prospective parents.