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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 file focusses on letter sent by Dr John Doncaster, Headmaster of Oakham School, regarding some pupils and staff matters. File dates from the first half of the 19th century.

This file focusses on letters sent or received by William Spicer Wood, Headmaster, in the mid-19th century.

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.

A modern transcript of a letter from William Spicer Wood, Headmaster of Oakham School, and Edward Thring, Headmaster of Uppingham School, addressed to the Governors of both schools regarding the relation between schools and their future as separate institutions.

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 file focusses on official reports published on the life at Oakham School in the 1860s.

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.