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This collection focuses on the administrative side of the school including admissions and trustees.

There is a rich collection of admissions books dating back to the 19th century alongside detailed notes of Trustees' committee minutes and development plans.

School inspections undertaken by external bodies are represented in this sub-fond and include some of the 19th century schemes which helped to found the school as one independent from Uppingham.

ADM/4 contains policy documents outlining the health and safety measures in the school.

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.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2018 and Spring term 2019. Contents: Farewell to Headmaster Nigel Lashbrook; Academic; Performing Arts; Trips and Tours; Geography Trip to Morocco; Geography Trip to Iceland; Pastoral; Activities; Sport; Staff News; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2014 and Spring term 2015. Contents: News; Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2003. Contents: Academic; Features; Societies; Party Time; Music and Drama; Art & Design; Pastoral; 20:20; The Old Oakhamian; Sport.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

The items in this file are related to the admission of girls in schools and the changes to school's curriculum, campus and rules.

A photograph of Elizabeth Inglis when she first came into Stevens House in the Winter term 1990.

This series is related to school fees and tuition. Items include reports from the Bursar on increase of fees, balance sheets, and individual pupils' bills.

A notebook with names and dates of entry for Common Entrance and Junior Entrance for girls and boys, day pupils and boarders, recording the entry fees. Nineteen pages A to S.