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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 file consists of various registration books, since the 1960s.

A green hardback book containing lists of day boys for the Junior Entry and Sixth form entry, from September 1987 to September 1998.

A photograph of the day boys in Barrow in the academic year 2007-2008 under the Housemaster Adam Williams.

A photograph of the Day boys in Sargants House in the academic year 2018-2019 under the Housemaster Ashley Denman. Names of pupils and staff are written below the photograph.

A brown notebook recording the performance of candidates who took the entrance examination between 1970 and 1978.