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This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

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 booklet produced by Davis Langdon & Everest for Oakham School on a first estimate for the Oakham Innovation Centre. Contents: Comparison between options, Summary of Estimate, List of drawings and other information, Exclusions, Schedule of Areas, Design Reserve and Contract Contingency, Inflation an Programme, Detailed analysis of construction costs.

This sub-series focusses on photographs of Oakham School 1st Shooting VIII, mostly during the 1950s and 1960s, as well as teams competing in the Ashburton Competition at Bisley.

An article published in The Independent on Sunday on the publication of a new book, "Wisden on the Great War", and focussing on the Oakham School 1st cricket XI of 1914 and the five boys in the team who fell in the Great War. The article is spread on two pages, numbered A and B.

Obituary of Rev Edward Vere Hodge from The Times Educational Supplement on 10 September 1932.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

This file focusses on photographs of G. Talbot Griffith, Headmaster of Oakham School.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).