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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.

A sermon preached by The Lord Bishop of Ossory, J.G.F. Day, on the occasion of the 350th anniversary of the Foundation of Oakham 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.

This file relates to the National Youth Orchestra, in particular their newsletters in 1993 and 1994, and their stay at Oakham School in August 1993.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

The Old Oakhamian Magazine, published in Summer 2000. Contents: Reunion of '80-'85; The Torch is on its Way; Paris Dinner; News of; A Century of Sporting Achievement; Roll of honour; Births, Marriages & Deaths; The Millennium Chapel Appeal; Obituaries; Database and Website.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2002. Contents: Features; Old Oakhamians; Academic; Arts; Pastoral; Sport; Services.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2004. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; The Old Oakhamian; The Foundation.