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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.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

This file focusses on various items relating to the history of Oakham School, its pupils and Old Boys, under the headmastership of Rev William Spicer Wood.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

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.

This collection focuses on the administrative side of the school including admissions and trustees.

There is a rich collection of admissions books dating back to the 19th century alongside detailed notes of Trustees' committee minutes and development plans.

School inspections undertaken by external bodies are represented in this sub-fond and include some of the 19th century schemes which helped to found the school as one independent from Uppingham.

ADM/4 contains policy documents outlining the health and safety measures in the school.

A book compiling the minutes of the Trustees' Financial Committee meetings.

This series relates to the Finance Committee of the Trustees, in particular minutes of their meetings.

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 roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.