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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.

A4 Magazine named "Oakhamian - October 1992", stappled; a photograph of a girl performing wearing of golden dress and a boy in a white shirt on the cover; 64 pages; contents: People Places Events, Drama, General, Tanzania Expedition, Houses, Speech Day, Music, Valedictory, Sport; with various photographs of staff, pupils, plays, sports, trips

A4 Magazine named "Oakhamian - February 1990", stappled; plain, grey cover with red letters; 52 pages; contents: Editorial, People Places Events, OSCA, Travel, Music, Drama, Talkback, Sport; with various photographs of staff, pupils, plays, sports, trips

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

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

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 156 Pages; Contents for the Oakhamian: The Headmaster writes, Read All about it, New Faces, A Year in Pictures, A Coronavirus Challenge, Academic, Performing Arts, Trips & Tours, Community, Activities, Sport, Beyond Oakham. Contents for the OO Club Magazine: News, Alumni Interview, Dairy Good, 1584 Society, Frank & Stuart, Nursing the coronavirus frontline, OO Entrepreneurs, Memories of Oakham, Pet Names, Obituaries.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 131 Pages; introduction to Mr Henry Prices as Head, painting, sculpture, textiles, an evening with Dr Venkatraman Ramakrishnan (noble prize winner), FOSIL investigation, Lower School, Modern Foreign Languages, Return to the Forbidden Planet, Alice's Adventures in Wonderland, music concerts, India 2019 trip, Lower school trip to France, Madrid 2019, Orielton 2019, Choir tour to Latvia, Lower 1 trps, Woolsthorpe Manor trip, Speech Day 2019, Sports days, House News, Leavers' Day, OSCA, CCF, Duke of Edinburgh, Sports, new staff arrivals, Careers. Accession Number 13102020/4.