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A letter from Roger Blackmore to Peter Gravells, Executive Chairman at Catering by County Ltd, regarding the ox roast letter, the Grand Ball letter and OSEL's demands.

A brochure advertising the International Chess Tournament at Oakham School, including a programme of the event, a map of campus, and photographs of previous competitions.

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 forecasting OSEL profits for the year 1993-1994.

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

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

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.

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

A collection of documents relating to the Wharton pavilion, built on the site of the Old Gymnasium, adjacent to Wharflands. The opening ceremony took place on 4 July 1983 by O.O. Ron Jacobs ('45), President of the R.F.U. In July 2014, the Wharton Pavilion, known as Stumps, was taken down.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.