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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 Spring and Summer terms 1987. Contents: Editorial; School News; Tributes to Retiring Staff; Industry and Oakham School; Some Reviews from "On the Road"; Drama; Music; Art and Design; Societies; Tours; Expeditions; D of E and C.C.F.; Sport.

A bound copy of several Oakhamian Magazines from Spring 1984 to Summer 1987.

The Oakhamian Magazine, recording the Spring and Summer terms 1985. Contents: Editorial; School News; Speech Day; Chapel; Careers & Business Studies Trips; The White Bix; Trips; Russia; Trinidad & Tobago; Australian Exchange; Drama; Blood Wedding; Hiawatha; The Cotchford Tales; Music; Societies; Art & Design Centre Activities; C.C.F. and DofE; Sport; Leavers' Destinations.