A letter from the Headmaster Graham Smallbone to Parents reviewing the Winter term 1992. Contents: The Future; Examination fees; Choral Society performance; Rutland - A Visitor's Guide; Three Special Requests; Responsibility for each other. Two pages A and B.

A letter from the Headmaster Henry Price to Parents regarding lockdown, and staff recruitment and changes.

A letter from the Headmaster Designate Henry Price to Parents regarding the Teacher Assessed Grades replacing external examinations in May 2021.

A letter from the Headmaster Henry Price to Parents regarding the disruptions to External Examinations after the announcement of lockdown in the UK in March 2020.

A letter from the Headmaster Nigel Lashbrook to Parents at the end of Spring term 2019. Contents: Examinations; Gala Concert; Decem; Brexit.

Notes by the Headmaster Graham Smallbone on the future needs of the School for a discussion in January 1986. Two pages A and B.

A headmaster's annual report for the academic year 1978-1979. Contents: Numbers; Academic; Careers; A.V.A. Centre; Library; Art & Design; Music; Physical Education; Sports Hall; Playing Fields; Shooting; Drama; C.C.F.; The Duke of Edinburgh's Award Scheme; Exploration Society; Scouts & Guides; Discipline and the Decem; The Houses; The Chaplaincy; Ashburton Hall; School Council; The Oakhamian; Senior and Middle School Societies; Voluntary Services; The Sanatorium; Oakham School Nursery; Old Oakhamian Club; Conclusion. Attached are A-Levels results (appendix A), O-Level results (appendix B), Summary of University applications and places gained (appendix C), a memorandum on Development of the Sargant Laboratories and a final report on Svalbard '79. Twenty-one pages A to U.

This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

A sermon given by Headmaster John Buchanan at a Junior Service on 15 June 1975, relating to examinations. The sermon is typed, with hand-written notations. Five pages A to E.

A calendar of events in the Summer term 1950. Three double-pages A to C.