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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.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

An end-of-term letter from the Headmaster Tony Little to Parents regarding a durgs search, debating, drama and music performances, sports successes

A letter from the Headmaster Tony Little to Parents regarding a review of the Spring term 2001. Contents: Sporting achievements; Debating; Arts, Music and Drama; Mobile Phones; Pubs, Clubs and Alcohol; Match Day Information; Summer term events.

An almost complete collection of the School's magazines dating from 1884.

A4 Magazine named The Oakhamian, stappled; a photograph of two cricket players tossing a coin on the cover; 31 pages; contents: Farewells, History, Science, Miscellany, Englsih, Languages, Art, Performing Arts, Sport, Houses, Miscellany; with various photographs of staff, pupils, plays, sports, trips, art works

Magazine named The Oakhamian, stappled; glossy cover with a photograph of Garry Kasparov and two pupils; 31 pages; contents: VIP Visitor, Gap Year, English, History, Community Service, Performing Arts, Art, Sports, Miscellany, Languages, Houses; with various photographs of staff, pupils, plays, sports, trips

Magazine named The Oakhamian, stappled; glossy cover with a photograph of a "dog" formed of found objects and welded pieces of scrap metal; 55 pages; contents: Editorial, OSCA, Speec Day, Chess, Drama, Music, French Trips, Leavers, Dublin, Duke of Edinburgh' Award Scheme, , A-Level Art & Design, Geography expedition to Morocco, Corsica '99, House Reports, Sports, Oakham School 2050; with various photographs of staff, pupils, plays, trips, sports

Magazine named The Oakhamian, stappled; glossy cover with a photograph of a DofE group in front of a mountain in the snow; 64 pages; 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 Millenium Summit; with various photographs of staff, pupils, plays, trips, sports

Magazine named The Oakhamian, stappled; glossy cover with a photograph of cellists and violinists; 64 pages; contents: Chapel, OSCA, Drama and Music, Art, Design and technology, Expeditions and Trips, Creative Writing, Sport, House Reports; with various photographs of staff, pupils, plays, trips, sports