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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 series focusses on staff leavers, including list of staff changes, invitations to Leavers' events and booklets celebrating staff's time at Oakham School

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

This series is made of registers, recording teaching and support staff who worked at Oakham School in the late 19th century-early 20th century.

This series is related to school fees and tuition. Items include reports from the Bursar on increase of fees, balance sheets, and individual pupils' bills.

This series focusses on Oakham School policies. The bulk of the series relates to the Staff code of conduct.

This series contains various internal policies communicated to staff by the Bursary, regarding managing the budget, expenditures and staff responsibilities.

This photographic series focuses on the history of the chapel since the laying of the foundation stone. It documents its building and opening, services held in the Chapel and objects used in everyday services.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

This series focuses on Peterborough House pupils and staff since its inception in 1966. Most of the series is made of house photographs, house magazines from the 1970s and various administrative documents.