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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.

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

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 1995. Contents: Farewells; English; Jerwoods in Paris; Science; Music; Performing Arts; Miscellany & Gap Years; Art & Design; Activities; Sport; Miscellany & Houses.

The Oakhamian Magazine, recording the Summer term 1988 (published in October 1988). Contents: Editorial; People - Places - Events; Drama; Speech Day; Oakham Association; Girls Self Defence Course; OSCA; Diana Ridley Pram Race; Biology Society; Life behind the Counter; Reflex Dance; The Mountain Year; Travel; Fashion Show; Sport; Music; On the Road.

The Oakhamian Magazine, recording the Summer and Autumn terms 1986. Contents: Editorial; School News; Departures; Miscellany - Features and Opinion; Drama; Music; Art and Design; Societies; Tours; Expeditions; Camps and Adventures; Work Experience out of School; 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.

A bound copy of several Oakhamian Magazines from Summer 1993 to Summer 1997.

The Oakhamian Magazine, recording the Summer term 1990 (published in October 1990). Contents: Editorial; People - Places - Events; OSCA; Music; Drama; Festival; Concert; Recital; Valete; Sport.

The Oakhamian Magazine, recording the Summer term 1991 (published in October 1991). Contents: People - Places - Events; Co-Education; Festival Music; Drama; Peterborough to London by Kayak; Speech Day; A Day in the Life Of Oakham School; Aerobathon; Music; Sport.