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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.

This collection consists of material which highlights the history of Oakham School. This includes monographs and research by various authors, as well as films and others audio and video recordings.

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.

The Book of Oakham School, title and badge in red, fair condition, spine fragile and damaged on 1 duplicate at the bottom. Preface by Walter Lee Sargant, history of the school including the founder, earlier history and a list of governors; with drawings of buildings. With 2 duplicates

Leatherbook, brown cover, with reproductions of rolls copy of the charter of Oakham and Uppingham schools and hospitals; with letter to W.L. Sargant regarding the rolls

A Sermon by J G F Day on the 350th anniversary of the founding of the school.

A brochure promoting the 1960s Development Campaign. Contents: Post war Development; The Development plan; The Cost; The Future; Administration of the Campaign; Method of Giving. Also inserted are a combined Deed of Covenant and Banker's Order form.

A collection of reproduced documents researched by Joe Donnelly from the school's and it's land's very early history. Short introduction and contents included.