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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

Two letters between the Headmaster Tony Little and O.O. Dennis Peacock regarding websites and an article published in 'Resident Abroad' in 1999.

A letter from the Headmaster Tony Little to Dennis Peacock regarding the Oakham School website.

A brochure on Welland Valley prep School, an intention which never happened but was endorsed by Oakham School, enclosing a note from the Headmaster Tony Little

This file focusses on various publications, internal and external, under Tony Little's headmastership.

A series of correspondance, menus and newspaper cuttings concering Garry Kasparov's visit to the school and the under 14 chess training session.

This sub-series focusses on the visit of Garry Kasparov to Oakham School on 6 November 1997, including photographs and administration for the visit.

Registrar's reports

A headmaster's annual report fro the year 1983-1984, including numbers, Academic, Careers, A.V.A. Centre, Library, Art & Design, Music, Physical Education, Sports Hall, Playing Fields, Shooting, Drama, C.C.F., The Duke of Edinburgh's Award Scheme, Exploration Society, Scouts & Guides, Discipline and the Decem, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results, leavers' destinations and academic scholarships

Annual report for the year 1974-1975, including the school numbers, staff changes, academic, faculty reports, chapel, library, drama, C.C.F., Scouts, DofE, Health, School council, Old Oakhamians, Oakham School Nursery Group, The International club, Accomodation, General. With an appendix: job description for public relations co-ordinator and conference organiser