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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 series relates to the history of Oakham School Exploration Society since its inception in Spring term 1978 until 1998. Most of the collection is made of expedition diaries and reports.

The series contains negative files produced by Roger Blackmore, showing pupils, staff, school campus and buildings, drama productions, sports competitions and other activities.

Various photographs, not related to any sub-fonds, and included in the larger Photographic Collection.

All the items in this series are related to the frescoes in Old School, commissioned by Walter Lee Sargant and painted by his sister, Mary Sargant-Florence, illustrating the "Story of Gareth".

This series contains legal documents on various themes, a court case and an insurance scheme.

The items in this series are books written and published by members of staff and are related to the history of Oakham School.

This series focusses on the history of Oakham School Politics Association, opened to pupils in the Upper School.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.