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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).

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

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 girl wearing a sliver-plated mask with rose quartz ear-piece; contents: Editorial, London Science Museum, R.A.F. trip to Hunstanton, Study Visit to Berlin, Drama, Art & Design in Paris, Sports, Alzira exchange, Travel, Houses ; with various photographs of staff, pupils, plays, sports, trips; one page has been torn

Magazine named The Oakhamian, stappled; glossy cover with a photograph of two hockey players including a goaly on the astro; 56 pages; contents: Editorial, Chapel, OSCA, Oxbridge, Concerts, Inner Cities Project, Drama, The Battlefields, The total Eclipse of the Sun, Russia, California, GCSE Design & Technology, Sports, Houses; with various photographs of staff, pupils, plays, trips, sports

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