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This sub-series contains photographs of the boys in Deanscroft. It covers the whole history of the boarding since its inception in 1948, up to 1988 when the boys were transfered to the new Haywoods house.

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.

This file contains photographs of the 1988 International Chess tournament held in the Sports Hall and the Ashburton Hall.

A brochure advertising the International Chess Tournament at Oakham School, including a programme of the event, a map of campus, and photographs of previous competitions.

A photograph of guests and participants at the 1984 International Junior Chess tournament organised as part of the Quatercentenary celebrations.

This sub-file contains various photographs of Jane Minshall (nee Charman).

Four identical letters (A to D) from Headmaster Graham Smallbone and four other members of staff - Roger Blackmore, Nigel Webb, John Buchanan and Rev Terence Treanor- to Old Oakhamians. Attached is a mailing list (E).

Two letters, from Trevor Case and Roger Blackmore to John Barber regarding the sums produced by the sales of signed copies of "The Story of Oakham School" to the Quatercentenary Appeal.

Two letters (A and B) to Roger Blackmore, new Chairman of the Holiday Lettings Committee, and to Nigel Webb, member of the Committee, regarding the new company and their new roles.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.