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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 Winter term 2003. Contents: Academic; Features; Societies; Party Time; Music and Drama; Art & Design; Pastoral; 20:20; The Old Oakhamian; Sport.

The Oakhamian Magazine, recording the Spring term 1996. Contents: History; English; Performing Arts; C.C.F.; Science; Miscellany; Geography; Gap Year; Art; Sport; Houses; Miscellany.

A bound copy of several Oakhamian Magazines from February 1988 to February 1991.

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

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.

Three photographs of the 2001 Lower School Sports Day winners and Lewis Moody handing the trophies.

A photograph of Diana Sowter receiving the Outstanding Sportswoman cup from O.O. Lewis Moody ('96) at the Lower School Sports Day in 2001.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2008. Contents: Staff News; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.