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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.

This sub-series focuses on photographs of the Day Girls in Gunthorpe since its inception in 1997 and contains all but one photographs of the Housemastership of Mary Grimley, only missing the year 2006-2007. It contains both formal and informal photographs as well as some photographs of the Sixth Form girls.