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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 focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

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

Magazine named "The Old Oakhamian", on paper; 4 pages; contents: Annual Dinner, Old Oakhamian Fund, Cricket, Football and Golf, School Notes, Births, Marriages and Deaths, In Memoriam, Old Oakhamian Notes, Notices

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.