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).

The Oakhamian Magazine, recording the Summer terms 1980. Contents: Editorial; School News; T.C.S.H.; Chapel Notes; Profiles; Correspondence; Creative Writing; Expeditions and Adventures; Art and Design; Music; Drama; Societies; C.C.F. and Duke of Edinburgh Award Activities; Sport; School Officials.

The Oakhamian Magazine, recording the Summer and Winter terms 1987 (published in February 1988). Contents: Editorial; People - Places - Events; J. Walton; The Chapel; Poem - Consideration; Speech Day; Into Industry; OSCA; Being New; Denis Giuseppi; The Ashburton; The Barraclough Opening; Kenya; Drama; Poems; Sport; The Tramp; The Oxbridge Lie; Music; Societies and Travel; 20 years ago.

The Oakhamian Magazine, recording the Spring term 1991 (published in May 1991). Contents: People - Places - Events; OSCA; Societies; Lectures; Drama; Project Trust; Travel; Music; Lenten Address; Sport.

The Oakhamian Magazine, recording the Spring term 1999. Contents: Editorial; Chapel; OSCA; Oxbridge; Concerts; Inner Cities Project; Drama; The Battlefields; The Total Eclipse of the Sun; Russia; California; GCSE Design & Technology; Sports; Houses.

The Oakhamian Magazine, recording the Spring term 2000. Contents: Editorial; Chapel; OSCA; Leavers 1999; Wordhoard; Music; Drama; Art & Design A-Level; Science Museum; Languages; Ski Trip; Operation Raleigh; Arran; Duke of Edinburgh Award; Battlefields Trip; Debating; Sport; House Reports; Chess; School Council; Model United Nations Millennium Summit.

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.

The Old Oakhamian Magazine, published in 1990. Contents: Summer Ball; A Proud Record; This Year's President; Annual Dinner; O.O. Day and A.G.M.; Regional Reunions; School News - Round-up; Endings; The Chapel;£50,000 in Five Years; Music; Drama; The Oakham Festival; C.C.F.; Duke of Edinburgh and OSEL;, Sport; Jolly Hockey Sticks; Wharflands in the Thirties; Wharflands in the Forties; Whatever happened to; Public School Reminiscences; Letters; New Members; Addresses; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; O.O. Sport; O.O. Lodge; Club Colours/School Shop; Notices; Diary Dates.

A bound copy of several Oakhamian Magazines from 1937 to 1941.