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

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-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 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 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.

An almost complete collection of the School's magazines dating from 1884.

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.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.