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This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

This collection focuses on the administrative side of the school including admissions and trustees.

There is a rich collection of admissions books dating back to the 19th century alongside detailed notes of Trustees' committee minutes and development plans.

School inspections undertaken by external bodies are represented in this sub-fond and include some of the 19th century schemes which helped to found the school as one independent from Uppingham.

ADM/4 contains policy documents outlining the health and safety measures in the school.

A headmaster's annual report fro the year 1983-1984, including 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, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results, leavers' destinations and academic scholarships

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

This collection highlights the depth and breadth of the school's curriculum and pupil's work. The drama and music sub-series are particularly detailed with their collection of production stills and programmes.

CUR/7 contains reports relating to the school's teaching and curriculum alongside timetables for lessons and exams, and comprehensive examination results for GCSE, A Level and IB.

Throughout the series in this collection, there is material relating to events and trips undertaken by various departments to increase the extra-curricular activities of pupils.

A confidential memorandum from T.M. Reay, Bursar, to Roger Blackmore and D.M.W. regarding the Chapel Choir CD.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

A letter from Roger Blackmore to Alan Grieve regarding the new OSEL letterhead.

A letter from Roger Blackmore to Alan Grieve regarding the 1985-1986 programme of activities and events organised by OSEL. Two pages A and B.

A letter from Roger Blackmore to Alan Grieve regarding attending a meeting of delegates from companies marketing Activity Holidays and OSEL being represented in a sub-committee.