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This collection highlights the depth and breadth of the school's curriculum and pupil's work. The drama and music sub-series are particularly detailed with their collection of production stills and programmes.

CUR/7 contains reports relating to the school's teaching and curriculum alongside timetables for lessons and exams, and comprehensive examination results for GCSE, A Level and IB.

Throughout the series in this collection, there is material relating to events and trips undertaken by various departments to increase the extra-curricular activities of pupils.

A speech given by Headmaster John Buchanan on Speech Day 1964, paying tribute to the late Chairman, Sir Eric Gore-Browne, discussing three reports on Education, examination results, Music and other activities, sporting achievements, boarding matters and the Development Campaign. The speech is typed, with hand-written notations. Six pages A to F.

A collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

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 series is related to the charity work at Oakham School, including the fund raising and other events organised at school by staff, pupils, houses and the Oakham School Charities Association (OSCA) in aid of various charities and the local community.