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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.

This sub-series focuses on photographs of boys, living in Junior House/Chapmans since its inception. The bulk of the collection gathers photographs from the 1950s to 1980s.

This sub-series focuses on photographs of girls in Orchard Close and Buchanans House, mostly in the 1990s and early 2000s. It also contains photographs of the Sixth Form cohort.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on obituaries and tributes written in memory of former Headmaster, John Buchanan, as well as letters from friends and family.

Two formal photographs of the girls in Orchard Close in the academic year 1976-1977, under the Housemaster Michael Stevens. The photograph A is in colour and mounted on a card board. The photograph B is in black and white and slightly different; a number of print is written on the back: O490/1.

An informal photograph of the girls in Orchard Close on the stone bridge in the academic year 1976-1977, under the Housemaster Michael Stevens.

A photograph of Oakham School teaching staff in the academic year 1984-1985. The photograph was taken in the Spring or Summer term 1985, under Acting Headmaster Michael Stevens.