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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.

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.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2016. Contents: News; Features; Academic; Performing Arts; Trips and Tours; Cover Story; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation; The OO Interview.

Minutes of an OSEL meeting held on 25 October 1983 at the Headmaster's house. Contents: Minutes; Matters arising; Medical Congress, January 1984; Chess Tournament; Other April events; Activity Holidays 1984; Computer Weekends; Catering budgets and menus. Seventeen pages A to Q.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

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.

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.

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.

A wooden trophy made to look like a scroll with a large metal medallion in the centre and seven small ones, of which four are engraved with the wining house and year. The trophy was for the interhouse public speaking competition. The list of winners is as follows: Stevens in 1992; Haywoods in 1993; Buchanans in 1994 and 1995.