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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.

This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

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

This sub-file contains various photographs of the girls in their boarding house, as well as various items recording the every day life and events in Buchanans House.

Three letters from Alan Grieve and Roger Blackmore regarding OSEL events and Activity Holidays in 1984 and the need to add to the catering staff.

A letter from Roger Blackmore to Alan Grieve responding to the memorandum AB/26/13/21 and giving feedback from an OO Committee meeting regarding the Dinner on 24 November.

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 letter from Roger Blackmore to Alan Grieve regarding a card to be sent to all Old Oakhamians and the catering arrangement for the OO Dinner.

A storage file with negatives of Roger Blackmore's photographs. A list of contents: OO dinner, Maintenance staff, Medical congress, fashion show, drama.