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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.

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.

A collection of material which focuses the school accounts and financial procedures over the years. This includes information on general accounts, pupil fees, committee minutes, staff wages, legal proceedings, and guidance policies for staff.

A green minute book recording minutes of working party meetings and general meetings of the Oakham School Foundation from the 2000s.

Two letters (A and B) between Jeremy Tomlinson, Bursar & Clerk to the Trustees, and Philip Robson at Daltons Solicitors, regarding the estate of the late John David Buchanan.

A balance sheet forecasting OSEL profits for the year 1995-1996.

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

A balance sheet on Oakham School Enterprises Ltd activities for the year ended 31 August 1995.

A balance sheet of the catering costs for Summer Holidays events in 1995.

A balance sheet forecasting OSEL profits for the year 1993-1994.