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A ltter from the Second Deputy J.M.D. West to Inspector A, Harrison to inform the local police of the Rutland Water Walk and that children will be walking on the public highway

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.

A letter about employment and general life news. Also contains details about the school nurse's death and an update on the school.

Two letters between the Headmaster Graham Smallbone and Idris Evans at Oakham Town Council regarding the Official Street Plan in September 1986.

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 file focusses on letters written or received by Walter Lee Sargant.

A letter from Michael Seivewright, Pubilc Relations Oficer at Rutland Stroke Club to the Headmaster Tony Little thankin him for the Harvest Party

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