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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 series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2017 and Spring term 2018. Contents: Features; Academic; Performing Arts; Cover Story; Trips and Tours; Pastoral; Sport; Staff News; Old Oakhamian.

A bound copy of several Oakhamian Magazines from Spring 2009 to Summer 2011.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2009 and Spring term 2010. Contents: Features; Staff News; Trips and Tours; Academic; Performing Arts; Pastoral; Community Activities; Sport; Beyond Oakham; Foundation; Old Oakhamian.

A bound copy of several Oakhamian Magazines from Spring 2007 to Winter 2008.

A bound copy of several Oakhamian Magazines from Spring 2005 to Winter 2006.

This sub-series contains letters related to School House. The items relate to the 2004 naming ceremony of rooms in School House.

A letter from Jon Wills, Chairman of the Old Oakhamian Club, to Lewis Moody ('97) regarding attending the opening of a room named after him in School House.

A letter from B.A.F. Smith ('54) to Jon Wills, Chairman of the Old Oakhamian Club, thanking him for the visit to School House and the naming of the rooms after his family.