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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 series focuses on the Junior Day boys' house of Sargants, since 1959. The main items are house photographs, photographs of the prefects and handbooks.

This series focuses on the Day boys of Clipsham, founded in 1997. The main items are house photographs and handbooks.

This sub-series focusses on handbooks written by the Housemasters, to welcome and help new Day boys or Prefects settling into their new environment.

This sub-series focusses on handbooks written by the Housemasters, to welcome and help new Day boys settling into their new environment.

This series focuses on the Day boys' house Barrow, founded in 1997. The main items are house photographs and handbooks.

This sub-series focusses on handbooks written by the Housemaster of Sargants, to welcome and help new Day boys or Prefects settling into their new environment, and inform parents and tutors.

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

A handbook for Sargants House to welcome new Day boys at the start of the 2003-2004 academic year, including list of tutors and prefects, information regarding the daily routine, the school day, activities and sports, rules of the house.

A handbook for Sargants House to welcome new Day boys at the start of the 2002-2003 academic year, including list of tutors and prefects, information regarding the daily routine, the school day, activities and sports, rules of the house, and a summer timetable.