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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 charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2017 and Spring term 2018. Contents: Features; Academic; Performing Arts; Cover Story; Trips and Tours; Pastoral; Sport; Staff News; Old Oakhamian.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

Notices compiled at the end of the Winter term 2018 and sent to Parents. Contents: Director of Operation's Notices; Registrar's Notices; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; School Archives; Art; Staff Changes. Two pages A and B.

This sub-series is made of items relating to the new Johnsons building, Faculty of Social Sciences, opened on 09 September 2017.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2016 and Spring term 2017. Contents: News; Academic; Trips and Tours; Performing Arts; Pastoral; Activities; Cover Story; Sport; Staff News; Old Oakhamian.

This file focusses on the official opening of the Faculty of Social Sciences on 9 September 2017.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2015 and Spring term 2016. Contents: News; Feature; Academic; Trips and Tours; Performing Arts; Cover Story; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation; The O.O. Interview.

A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.