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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 file focusses on various photographs of Richard Bull during his headmastership (1977-1984).

Two photographs of the School Choir with Peter Witchell. The photographs A and B show the same group of pupils but are slightly different.

A photograph of the School Choir with Peter Witchell. the photograph was taken by Brian and Elizabeth Nicholls and the number of print is written on the back: W183/6.

A photograph of the School Choir with Peter Witchell. The photograph was taken by Brian and Elizabeth Nicholls and the number of print is written on the back: AA157/3.

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.

Two black and white photographs of the new Peter Collins organ soon after its building in the School Chapel. The photographs A and B are identical but of different size.

Two photographs (A and B) of Oakham School Nursery children and staff in 1990. The photographs were taken by Brian and Elizabeth Nicholls and the number of print is written on the back of photograph A: CC170/1. Names are written on the back of photograph B.

A photograph of Oakham School Nursery children and staff in 1987. The photograph was taken by Brian and Elizabeth Nicholls and the number of print is written on the back: HH62/1.

A photograph of Oakham School Nursery children and staff in 1987. The photograph was taken by Brian and Elizabeth Nicholls and the number of print is written on the back: JJ80/3.