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This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

The Oakhamian Magazine, recording the Summer terms 1980. Contents: Editorial; School News; T.C.S.H.; Chapel Notes; Profiles; Correspondence; Creative Writing; Expeditions and Adventures; Art and Design; Music; Drama; Societies; C.C.F. and Duke of Edinburgh Award Activities; Sport; School Officials.

The Old Oakhamian Magazine, published in September 1993. Contents: Annual Dinner 1993; Time for a Change?; This Year's President - On the Move; O.O. Dinners; O.O. Day; Reunion; School News - Round-up; Oxford and Cambridge Results; Chapel; O.S. Charities Association; Music; Drama; Duke of Edinburgh's Award; School Sport - our finest year?; Cate's China; Phil's Japan; Engagements, Marriages, Births & Deaths; Obituaries; O.O. News; O.O. Sports; O.O. Lodge; Club Colours; Addresses of Members; Half a Century Ago; Celebration of Rutland; Notices; Diary Dates.