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A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

This file focusses on various documents relating to the history of the C.C.F. and the School Cadets, which do not fit in any other theme file.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A letter from Joan Armstrong at Taylor Garrett, on behalf of Alan Grieve, to Roger Blackmore regarding the OSEL prospectus and the figures for the Christmas conferences.

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

A letter from Joan Armstrong to Roger Blackmore acknowledging receiving his latter of 17 June.

A letter from Alan Grieve to John Buchanan regarding the 1986 International Chess Tournament. Two pages A and B.

A group of four letters relating to a proposal for a 'Careers in Medicine' video, a project proposed by John Metcalfe at The Royal Society of Medicine.

Two letters between Roger Blackmore and Alan Grieve on various matters, such as the last OSEL meeting, the new brochure for the Medical Congress and OSEL accounts.