This collection focuses on the pastoral and medical care for pupils and staff at Oakham School.

This includes a sub-series donated by Jane Matthews, the first female deputy head of the school. Her collection contains minute and administrative documents relating to maternity leave, girl boarding and tutorials.

Particular strengths of the collection are the patient books in PMC/2. There are record collated by the sanitorium and subsequent medical centre, as well as accident diaries and medical administrative documents.

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.

A book recording the baptism and confirmation services and candidates since 1972 (CHA/1/4/1/A). Some loose pages include a list of children baptised in 2008 and names of their parents, godparents an officiating minister, an email and application forms for baptism from 2003. Nine loose pages B to J.

This series contains items created or sent by the Sanatorium/Medical Centre. They are medical diaries, accidents books and various policies aimed at staff and houses.