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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.

A collection of photographs and art work of the Barraclough Dining Hall. It was opened on 28 September 1987 by Lord Forte. It contained two dining halls on the ground floor and a staff dining hall, bar and common room above. It was named Barraclough Hall, in memory of Norman Barraclough (OO, 1883) and his widow, Mrs Barraclough, a great benefactor to the school.

4 photographs in black and white of Eddie Willows's retirement: on a bike amongst staff, during Trevor Case's speech

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.

A box of ephmera from Buchanan's House.

This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.

Photographs, negatives and an order of service connected to the inaugural performance and dedication of the new chapel organ.

Minutes from the committee meeting including a discussion on double breasted blazers, new committee colours, and the possibility of banning golf.

A guest list and a photograph of the Deanscroft-Haywoods transfer and the Deanscroft 50 years anniversary.

A headmaster's annual report fro the year 1981-1982, 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 and leavers' destinations