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This collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

A collection of photographs and art work of School House, and plans of the building.

This file contains various plans of the buildings of School House and Old Hall.

This collection contains material relating to the history of the houses and their pupils. Each series is focused on a different house and many contain rich and detailed photographic records of houses year by year. Some houses are more detailed than others.

Other highlights of this collection include house handbooks, which help to induct a pupil into a house and its daily routine; photographs of daily life, including house events and leisure time; and administrative documents such as house diaries which record the calendar of house events, achievements of pupils, and accounts of incidents.

Included in this sub-fonds are houses which are no longer in existence such as Johnsons and Ruddles.

A list of the Housemasters of School House from 1951 to 2001.

This file relates to the Headmaster's Annual report to the Trustees, from the 1950s to 1980s. The reports cover all aspects of School, academic, examination results, extra-curricular activities, Estates and Maintenance, staff and individual faculty report, vision for the future of the School. All reports are private and confidential.

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 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.

Minutes of a Parent/Teacher Committee meeting held on 25 November 1978 at the Headmaster's house. Contents: Matters arising from the minutes; Careers; Speech Day and the end of the Summer term 1979; Any Other Business; Representation of the Committee; Date of the next meeting. Two pages A to B.

This file focusses on letters sent by Headmaster Richard Bull during his headmastership (1978-1984). The bulk of the collection is made of letters sent to Parents.