A headmaster's annual report for the academic year 1980-1981. Contents: Registrations/Entry; The Upper and Middle School Houses; Jerwoods; Discipline; Staff; General Academic; The Departments; A-Level and O-Level; University Entrance; The Library; Drama; P.E. and Sport; Sports Centre; Chapel; Voluntary Service; C.C.F.; Duke of Edinburgh Award Scheme; Exploration Society; Sea Scouts and Guides; Senior Societies and Middle School Societies; Careers; Publicity and Local Relations; Audio-Visual Aids Centre; The Oakhamian; The Ashburton Hall; School Council; Sanatorium; Old Oakhamian Club; Oakham School Nursery; Postscript. Seventeen pages A to Q.

The Oakhamian Magazine, recording the Summer term 1958 (published in Winter term 1958). Contents: School News; Avete; House Transfers; Valete; What is Toc H?; 21 Club; Chess; The Field Society; Stamp Club; The Band; O.P.R.S.; Lectures; O.S.M.A.S.; The Concert Club; Scout Notes; Film Notes; Showtime; Corps Notes; Bisley 1958; Problem Corner; Bert Cutting; The Brussels Exhibition; Rugger Forum; Trouble Brewing; Athletics; The Steeplechases; Swimming Sports; Cricket; Football; Hockey Fixtures; Correspondence; O.O. News. Eleven double-pages A to K.

The Old Oakhamian Magazine, published in 1952. Contents: Editorial; The Annual Dinner; Quinquennial Meeting; Regional Meetings; O.O. Golfing Society; School News; O.O. Notes; Engagements, Births, Marriages & Deaths; Obituaries; Notices; Correspondence. Two double-pages A and B.

The Oakhamian Magazine, recording the Winter term 1939 (published in Spring term 1940). Contents: Editorial; School News; Music; School Societies; O.T.C.; Scouts; Hockey; Cross Country Running; Rugby Football; O.O. News; War List; Roll Of Honour; The River Plate; Turkey at Easter; Cricket Fixtures. Item belonged to R.K. Sprigg. Six double-pages A to F.

A prospectus promoting studying at Oakham School in 1937. 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 are a form of application for admission (J) and a clothes list for the Junior House (K).

A bound copy of several Oakhamian Magazines from 1935 to 1937.

A letter from the Headmaster Graham Smallbone to O.O. Corinna Pike regarding the frescoes in Old School and the forthcoming Old Oakhamian Dinner.

A poster advertising an Oakham School Medical Society event with Old Oakhamians discussing Medicine careers held in the Wilson Auditorium on 23 March 2022.

A letter from Roger Blackmore to Alan Grieve regarding a card to be sent to all Old Oakhamians and the catering arrangement for the OO Dinner.

A letter from Jon Wills, Chairman of the Old Oakhamian Club, to Lewis Moody ('97) regarding attending the opening of a room named after him in School House.