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This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

A letter from Roger Blackmore to Trevor Case, Bursar, regarding OSEL accounts in 1985, payments, Commemorative items for the Quatercentenary and the OO dinner. Two pages A and B.

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 complete collection of Red Books - School lists and Calendars since 1959. Red books give information regarding pupils, tutor groups, teaching and support staff, school calendar and events, school rules, future trips and dates. Only two Red Books were never published, Summer term 2020 and Spring term 2021 as the UK was in lockdown (COVID-19) and pupils were not at School and had lessons online.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

A headmaster's annual report for the academic year 1983-1984. Contents: Numbers and Recruitment; Discipline and Morale; Staff; Academic; Art/Design/Music/Drama; P.E./Sports/Games/Service/Activities; Chapel; Food/Health; Careers/A.V.A.; Oakhamian/School Council; Publicity and P.R.; 1984 and All That. Attached are A-Level results (appendix A), O-Level results (appendix B), Academic Scholarships and Exhibitions (appendix C). Nine pages A to I.

A letter from the Headmaster Tony Little to Nigel Richardson, Headmaster of the Perse School, regarding the Golden Jubilee and sending photographs of the Queen's visit in 1984.

Correspondence between HMC Schools regarding the Golden Jubilee in 2002.

Minutes of a Parent/Teacher Committee meeting held on 10 March 1984 in Old Hall. Contents: Matters arising from the minutes; Boarding/Day Accommodation; Sub-Committee on Parent/Teacher Activities; Times of Parent/Teacher Evenings; Any Other Business; Representation of the Committee; Date of the next meeting. Four pages A to D.

Minutes of a Parent/Teacher Committee meeting held on 27 October 1984 at the Headmaster's house. Contents: Matters arising from the minutes; Visit of Her Majesty The Queen on 16 November; Any Other Business; Representation of the Committee; Date of the next meeting. Two pages A to B.