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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.

Magazine named "The Old Oakhamian", on paper, stappled; 4 pages; contents: Annual Dinner, Old Oakhamian Fund, Cricket, Football and Golf, School Notes, Births, Deaths and Marriages, O.O. Notes, New Members, Changes of Address, Notices, School Football Fixtures, Correspondence

A5 magazine, green cover; 63 pages; contents listed on the cover: Frontpiece, Editorial, Names and Addresses of Members, Annual Dinners, Headmaster's Letter, Mr. J. Story's Letter, Quinquennial Luncheon and Meeting, Resignation of Mr. W.L. Sargant - An Appreciation, "The Captain of the Ship", Presentation to Mr. W.L. Sargant, Cambridge Letter, The Book of Oakham School and The Register, Births, Marriages and Deaths,Cricket, Football and Shooting Matches, The Golfing Society, Club Notices, School Staff; with a photograph of Scriven, Douglass, Jerwood, Sragant, Hodge and Mrs Hodge

A5 magazine named The Oakhamian, stappled; 30 pages; contents on the inside cover: School Officials, School Notes, Obituary, the Chapel, Music Notes, the Library, Photographic Society, Debating Society, Reading Society, the Needle's Eye, Cricket, Swimming, Football, Boxing, the Scouts, Poem - Matin

This file focusses on roll call lists from the late 19th century/early 20th century, under the headmastership of Rev Edward Vere Hodge.

Staff and Trustees list and school roll per forms, including successes at the Royal Drawing Society Exam and Oxford and Cambridge examinations. Items A to E

Staff and Trustees list and school roll per forms, including successes at the Royal Drawing Society Exam and Oxford and Cambridge examinations. Cover detached from the booklet. Items A to E

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

A roll call of the summer term including names of trustees, teachers, upper, middle and lower school, and prizes given out for subjects and awards. Items A to E

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.