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The items in this series are related to Pastoral Care at Oakham School. Various topics include wellbeing, resources for tutorial, discipline and school rules, child protection and staff training.

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

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

This series contains monographs written, updated and produced by Brian Needham, Honorary School Historian, regarding various themes of the history of Oakham School, its pupils and teachers.

This series focusses on the headmastership of Rev Robert Tabraham (1875-1878) and of Rev Henry Walter Fitch (Acting Headmaster, 1878) and contains items relating to the life at School in the second half of the 19th century.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This series focuses on the Millennium celebration which took place in the School Chapel, with an emphasis on the candelabras (objects and photographs) designed and made by the Art & Design Department for the special occasion.

This series contains various recording materials related to some years at Oakham School.

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