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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 sub-file focusses on the stay of the National Youth Chamber Orchestra at Oakham School in August 1993, including details of the arrangements, correspondence, and programmes of their performances at Peterborough Cathedral, The Maltings, Oakham School Chapel, and The Proms at the Royal Albert Hall.

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.