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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 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.

A photocopy of a cutting from a history regarding an Usher Report mentioning numbers, fees. Possibly from Wood's headmastership. Hald of the article is missing.

Magazine named The Oakhamian, stappled; plain white cover; 62 pages; contents: School News, Correspondence, Drama, Music, Magic Mother's Problem Page, the Athelings Canadian Tour, Careers, Poetry, Games, C.C.F., Scouts, Avete, Valete; with a photograph of: the Duke of Edinburgh, girls playing rugby, CCF camp, a couple in the library, the Army summer camp

An early photocopy of the terms (fees) and endowments of Oakham School with hand-written note at the bottom.

Lent term bill for Donald at Junior House for pocket money, book account, music lessons, clothes, stamps...

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

Speech notes for the speech day on 1963. Handwritten annotations. Items A to F

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.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.