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

A prospectus promoting studying at Oakham School in 1942. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; O.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Nine double-pages A to I. Enclosed is modifications to the clothes list due to Rationing in July 1941 (J).

Issue of The Old Oakhmian Calendar. Contents: Frontpiece, Editorial, Names and Addresses of Members of the Old Oakhamian Club, Annual Dinners, Presentation to Mr. J.C. Clark, The Headmaster's Letter, Cambridge Letter, Review of School Games 1924-1927, Mr. J.C. Clark's Trip to Canada, Births, Deaths and Marriages, Old Oakhamian Notes, Cricket and Football Matches, School Staff Sept. 1927; with a photograph of the West Front of the Memorial Chapel; with hand-written amendments to the Members' list. Double-pages numbered A to M.

The Oakhamian Magazine, recording the Spring term 1989 (published in May 1989). Contents: Editorial; People - Places - Events; OSCA; Travel; Nostalgia; Societies; Music; Drama; Sport.

Old Oakhamian Calendar, published in 1927. Cover with contents: Frontispiece; Editorial; Names and Addresses of Members of the Old Oakhamian Club; Annual Dinners; Presentation to Mr J.C. Clark; The Headmaster's Letter; Cambridge Letter; Review of School Games, 1924-1927; Mr J.C. Clark's Trip to Canada; Births, Deaths and Marriages; Old Oakhamian Notes; Cricket and Football Matches; School Staff - September 1927. Thirteen double-pages A to M.

A bound copy of several Oakhamian Magazines from 1902 to 1910.

A bound copy of several Oakhamian Magazines from 1914 to 1916.

A bound copy of several Oakhamian Magazines from February 1988 to February 1991.

This sub-series related to the weekly services at the School Chapel since it being built in 1925. The registers record confirmation and baptism services as well as Carol services, evensong, matins and holy communion services.

An O.T.C. account book recording receipts and expenditure from 1912 to 1938.