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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.

The Oakhamian Magazine, recording the Summer term 1995. Contents: Farewells; English; Jerwoods in Paris; Science; Music; Performing Arts; Miscellany & Gap Years; Art & Design; Activities; Sport; Miscellany & Houses.

The Old Oakhamian Magazine, published in 1985. Contents: 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; An Oakham Overture to Poetry. Twenty-three double-pages A to W.

A bound copy of several Oakhamian Magazines from February 1988 to February 1991.

The Oakhamian Magazine, recording the Winter term 1980 (published in February 1990). Contents: Editorial; People - Places - Events; OSCA; Travel; Music; Drama; Talkback; Sport.

The Oakhamian Magazine, recording the Summer term 1992 (published in October 1992). Contents: People - Places - Events; Drama;General; Tanzania Expedition; Houses; Speech Day; Music; Valedictory; Sport.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Summer term 2019. Contents: Feature; Academic; Performing Arts; Trips and Tours; Pastoral; Cover Story; Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian.

The Oakhamian Magazine, recording the Summer term 1994. Contents: Speech Day & Places '94; Farewells & Places '93; English; Languages; Houses; Travel & Adventure; Performing Arts; DofE Canoeing; Art & Design; Sports; Miscellany & Editorial.

The Oakhamian Magazine, recording the Summer term 1997. Contents: Farewells; Jerwoods Activities; Languages; Science; Art; Sport; Geography; Miscellany; Performing Arts; Houses; Miscellany.

A bound copy of several Old Oakhamian Magazines from 1985 to 1990.