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 Winter term 2002. Contents: Features; Old Oakhamians; Academic; Arts; Pastoral; Sport; Services.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Spring term 2006. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Summer term 2006. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Spring term 2008. Contents: Features; 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 The Old Oakhamian Magazine, recording the academic year 2020-2021. Contents: The Headmaster Writes; News; New Faces; New Roles; Cover Story - Together Apart; Academic; Performing Arts; Trips and Activities; Community; Sport; Old Oakhamian.

The Oakhamian Magazine, recording the Winter term 2001. Contents: Chapel; OSCA; Music and Drama; The Millennium Sculpture; Art; Design and Technology; Expeditions and Trips; Sport; House Reports.