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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 covers the charity and outreach work undertaken by Oakham School's staff and pupils.

There are sub-series focusing on OSCA (the school's charity association), the Rutland Water Walk, Voluntary Action, and interaction with local prep schools.

Photographic and administrative material are particularly dominant in this sub-fonds.

A balance sheet detailing the funds raised by each house during the year 1992-1993.

A poster advertise the Christmas Jumper Day to be held on 10 December 2021 at school in aid of Oakham's PHAB Group.

The financial regulations policy for Oakham School, the Foundation and OSEL, including staff responsibilities, risk assessment, budget, planning, fraud and corruption, reporting, income, expenditure and income generation.

This subfonds contains the Archive's complete collection of Red books. These books contain a calendar of events for the upcoming term, lists of pupils and their houses, and lists of staff.

Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.