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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.

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 sub-file is made of two letters between O.O. Alwyne Westmoreland ('32) and the Headmaster, John Buchannan, regarding the forthcoming Development Campaign.

This sub-file focusses on two letters bet the Headmaster, John Buchanan, and O.O. Alwyne John Westmoreland ('32) regarding Oakham School winning the Ashburton Shield in 1966.

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.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

This file focusses on letters sent/received by G. Talbot Griffith.