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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 collection of material which focuses the school accounts and financial procedures over the years. This includes information on general accounts, pupil fees, committee minutes, staff wages, legal proceedings, and guidance policies for staff.