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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 series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This series focusses on the history of Oakham School Nursery, established for staff children. Most of the items are photographs from 1987 to 2001, when the Nursery was closed.