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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 sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

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.

A collection of documents, including photographs and commemorative plaques, relating to the Sports Centre, opposite Wharflands, opened in Winter 1972. A new modern indoors swimming pool was built in 1976.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

This file contains various documents and articles pertaining to the history and the architecture of College House.

A detailed description of the walls, roof, windows and floors of College House and mention of any damage to the structure, by R.E.M. Thomas, School Marshal, in February 1998. Three pages A to C.

Three letters from R.E.M. Thomas, School Marshal, to Cecil A. Hewett (A), Professor James Stephen Curl (B) and David Watt (C) regarding the architecture of College House and a comparison with Quaintree Hall in Braunston.

A detailed description of the walls, roof, windows and floors of College House and mention of any damage to the structure, by R.E.M. Thomas in February 1998 and an addendum from May 1998. Four pages A to D.

A list of School buildings and their dates of construction and contractors compiled by R.E.M. Thomas, School Marshal, and other town buildings. Two pages A and B.