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This collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Spring term 2009. Contents: Features; Staff News; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

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.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2010 and Spring term 2011. Contents: Staff News; Features; Trips and Tours; Academic; Performing Arts; Pastoral; Community Activities; Sport; Foundation; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2011 and Spring term 2012. Contents: Staff News; Features; Trips and Tours; Academic; Performing Arts; Pastoral; Community Activities; Sport; Foundation; Old Oakhamian.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2012. Contents: Staff News; Trips and Tours; Features; Academic; Performing Arts; Pastoral; Community Activities; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2013. Contents: Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; The Old Oakhamian Magazine; Foundation.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2013 and Spring term 2014. Contents: News; Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2014. Contents: News; Features; Academic; Performing Arts; Jerwoods; Trips and Tours; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2014 and Spring term 2015. Contents: News; Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.