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This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

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.

This file focusses on correspondence regarding the refurbishment of Old School in the late 1980s-early 1990s and the issue concerning the frescoes.

A fax transmission from Bond & Read, Chartered Architects, to The Bursar Tom Reay, enclosing a letter from English Heritage to the Philip Dales at Rutland District Council, regarding the refurbishment of Old School and protecting the frescoes. Three pages A to C.

A letter from Carol Purcell at the Department of National Heriatge, to the Headmaster Graham Smallbone replying to a previous letter and consulting the local authority.

A letter from Roger Blackmore to Alan Grieve, Chairman, regarding OSEL accounts in 1985. Two pages A and B.

A letter from Joan Armstrong to Roger Blackmore acknowledging receiving his latter of 17 June.

A letter from C.H. Gadney, newly appointed Chairman of the East India, Sports & Public Schools Club, to John Buchanan regarding a member representing Oakham School in the Club Committee, using the Club's facilities, and the support and links between the School and the Club. Two pages A and B.