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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 transcript written by John Barber in 1992 of F.C. Doherty's pamphlet published in 1932, titled 'The Story of Oakham Church, School and Castle', price sixpence. A copies are almost unattainable, Mr Barber wrote a copy to be kept permanently in the School Archives. Three pages A to C.

Issue of The Grantham Journal reporting of the visit of His Royal Highness The Duke of Edinburgh to Oakham School on 8 November 1957. Three double-pages A to C.

A copy of 'The Co-Education Story' written by John Buchanan discussing the introduction of girls in 1971. Item was printed for a family reunion to celebrate 30 years of Co-Education. Fifteen pages A to O.

An article written by former Headmaster John Buchanan in 1980, detailing the configuration of the School and the Technology block. Two pages A and B.

Newspaper cutting from The Grantham Journal, reporting on the 1929 Speech Day and W.L. Sargant's retirement. Includes a detailed list of Honours and Prizes.

Issue no. 462 of The Rutland Times, Independence Souvenir Special, with reports on the celebration of the independence of Rutland. Thirteen double-pages A to M.

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 Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This file focusses on research and textbooks relating to Oakham School in the 19th century, under the headmastership of Dr John Doncaster.