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A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

An invitation card from the Headmaster and Mrs Lashbrook to the retirement dinner for Mr Jon Wills at Deanscroft on 21 June 2018.

This file relates to the opening and renaming of new dorms in School House and shows families and friends of Old Oakhamians cutting the ribbons and the following celebration in the small Barraclough and in Stumps.

Print outs of the photographs of the rededication service of the Chapel and the opening of Littles house on 30 September 2007. Twenty three pages A to W.

Order of service of the service of thanksgiving for the lives of Anna Haefeli and Anastasia Besedovska held at the Chapel on 17 January 2015.

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.

This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

A programme for the Oakham Fashion Show held in the Sports Hall on 18 March 2006 in aid of the Make-A-Wish Foundation.

A menu for Buchanans and Haywoods Sixth Form Guest Night held on 22 January 2011 in the Barraclough. With signature of some of the attendees.

This collection draws together material produced for and by the marketing department of Oakham School. Particular strengths of the collection include press cuttings and publication material (prospectuses, handbooks, maps etc.).

Press cuttings from multiple local and national newspapers have been collected together by marketing staff, gathering together news of Old Oakhamians.

Publications contain material produced for new admissions into the school and contain detailed information about uniform, curriculum, pastoral care, and general daily life of the school.