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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.

A5 magazine, red cover with the badge of the school on the cover; 85 pages; contents listed inside: Editorial, This Year's President, Richard Bull, O.O. Quatercentenary Dinner, A.G.M. and O.O. Day, Regional Reunions, 1984 - A Personal View, The Royal Visit, A Pilot through the Shoals, Life in the Twenties and the Eighties, School News, O.O. News, New Members, Address Changes, Engagements, MArriages, Births, Deaths, Obituaries, O.O. Golfing Society, O.O. Rifle Club, O.O. Masonic Lodge, Notices, Club Colours/School Shop, Rugby Fixtures, Diary Dates, Late News, J.D.B.'s "An Oakham Overture to Poetry", Centre Section - Oakham School Campus 1985; with photographs of the Royal Visit, portraits of Graham Smallbone, S.G. Schanschieff, a photograph of 5 old masters; with a loose document:a programme of the Old Oakhamian Day 08/06/1985; bottom o page 77 has been cut off

Bound Copy of several Old Oakhamian Issues; red, hard cover

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 focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

Four photographs of five people posing in front of the new Peter Collins organ in the School Chapel. They are (L to R): Peter Collins (Builder), David Woodcock (Head of Music), Peter Hurford (Organist), Graham Smallbone (Headmaster) and Simon Schanschieff (Chairman of the Trustees). The photographs are all slightly different (A to D).

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.