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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 sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

A collection of invitation and programme for the C.C.F. Biennial Inspection on 5 May 2006, as well as correspondence from the Foundation to guests, and letters from guests to the School regarding the event.

This sub-series focuses on letters related to the history of Wharflands house, its pupils and staff.

A page from "The Stag" comprising letters from Men on Service, including a note from Colin Francis Scott.

This file focuses on correspondence asking/ giving John Barber permission to use certain material in his book.

This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

This file focusses on letters and cards relating to Oakham School, sent/received under the headmastership of Rev Vere Hodge.