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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 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 School list of staff and pupils for the Summer term 1901. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1900; Oxford & Cambridge Board; Drawing Examination. Five double-pages A to E.

A School list of staff and pupils for the Summer term 1902. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1901; Oxford & Cambridge Board, 1902; Royal Drawing Society. Five double-pages A to E.

A School list of staff and pupils for the Summer term 1903. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1902; Oxford & Cambridge Board, 1903; Royal Drawing Society. Five double-pages A to E.

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

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Spring term 2008. Contents: Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2017 and Spring term 2018. Contents: Features; Academic; Performing Arts; Cover Story; Trips and Tours; Pastoral; Sport; Staff News; Old Oakhamian.

The Oakhamian Magazine, recording the Winter term 1999. Contents: Editorial; Chapel; OSCA; Drama; Music; Rocket to Mars; Simon Schanschieff; Geography Field Course; New York, New York; Berlin; Barcelona; Eastern Europe; Togo; Art and Design; Sport; House Reports; Seventh Form Leavers.

The Oakhamian Magazine, recording the Summer term 1945 (published in Winter term 1945). Contents: Roll of Honour; Editorial; School News; War Memorial Fund; A.T.C.; J.T.C.; Scout Notes; Music Notes; Captain W.D. Johnson; Swimming Sports; Football; O.O. Notes. Item belonged to D.J. Stocks in Junior House. Six double-pages A to F.