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This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

Two letters, from Trevor Case and Roger Blackmore to John Barber regarding the sums produced by the sales of signed copies of "The Story of Oakham School" to the Quatercentenary Appeal.

This collection draws together material produced for and by the marketing department of Oakham School. Particular strengths of the collection include press cuttings and publication material (prospectuses, handbooks, maps etc.).

Press cuttings from multiple local and national newspapers have been collected together by marketing staff, gathering together news of Old Oakhamians.

Publications contain material produced for new admissions into the school and contain detailed information about uniform, curriculum, pastoral care, and general daily life of the school.

A letter from Roger Blackmore to David Loveday regarding the arrangements and organisation of the 1993 Oakham Festival.

A note from Roger Blackmore to Andrew Keenan regarding the catering arrangements for the matinee performance of 'Cabaret' on 21 June 1992.

A fax from Roger Blackmore to Waite, Dodds & Waite confirming their order for buffet supper in the Festival Marquee on 26 June 1992.

An asset register of Oakham School Enterprises Ltd, from 1979 to 1993. Five pages A to E.

This sub-file is made of two letters from Roger Blackmore regarding OSEL accounts for the year 1984-1985.

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