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This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

A collection of photographs and art work of the Barraclough Dining Hall. It was opened on 28 September 1987 by Lord Forte. It contained two dining halls on the ground floor and a staff dining hall, bar and common room above. It was named Barraclough Hall, in memory of Norman Barraclough (OO, 1883) and his widow, Mrs Barraclough, a great benefactor to the school.

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

A photograph (A) of Oakham School Shooting team that won the Ashburton Shield in 1975. Attached is a list of names (B).

This file focusses on art work, including architect drawings, of the Barraclough Dining Hall.

Photographs and negatives of the 1989 annual Jerwood International Youth Chess Tournament held in the Sports Hall.

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.

A draft agenda and notes for a Holiday Lettings Committee meetings in 1978. Three pages A to C.

A brochure promoting OSEL Activity Holidays in Summer 1987, including information on the accommodation, food, costs and a list of all the activities and sports available.

A report on OSEL's Activity Holidays in the year 1986-1987, including payments and balance sheet.