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A headmaster's annual report for the academic year 1981-1982. Contents: Registrations/Entry/Numbers; The Upper and Middle School Houses; Jerwoods; Discipline and The Decem; Staff; General Academic; The Departments; A-Level and O-Level; Scholarships; University Entrance; Careers; The Library; Drama; P.E. and Sport; Sports Centre; Chapel and the Chaplaincy; Afternoon Activities; Voluntary Service; C.C.F.; Duke of Edinburgh Award Scheme; Exploration Society; Scouts and Guides; Senior Societies and Middle School Societies; Publicity and Local Relations; Audio-Visual Aids Centre; The Ashburton Hall;
The School Council; The Oakhamian; Sanatorium; Old Oakhamian Club; Oakham School Nursery; Postscript. Attached are A-Level results (appendix A), O-Level and A-Level results (appendix B), University Entrance (appendix D). Nineteen pages A to S.

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

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 menu for the C.C.F. Regimental dinner on 21 April 2016, including the music programme.

A menu for the C.C.F. Regimental dinner on 8 May 2019.

A menu for the C.C.F. Regimental dinner on 6 May 2014, including the music programme.

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

Oakham School Magazine, recording the Winter term 1895 (published in Spring term 1896). Contents: Editorial; School Notes; Gymnasium; Football "Nines"; The Concerts; Old Oakhamian Club; Staffa and Iona; A Carnival at Carlsruhe; Football; Correspondence. Seven double-pages A to G.

Oakham School Magazine, recording the Winter term 1896 (published in Spring term 1897). Contents: Editorial; School Notes; Gymnasium; Concert; Old Boys' Club; Beards; Football; Correspondence. Seven double-pages A to G.

Oakham School Magazine, recording the Spring term 1924 (published in Summer term 1924). Contents: School Notes; Quinquennial Meeting of the Old Oakhamians; The New Classrooms and Laboratories at Wharflands; The Chapel; The Debating Society; The Cross Country Steeplechases; Cricket Fixtures and the Sports; Lectures; Dramatic Performances; O.T.C. Notes; Boxing; Fencing and Physical Training; Games Account - Balance Sheet for 1923. Five double-pages A to E.