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This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

The Old Oakhamian Magazine, published in 1984. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; Oakham's Earliest Headmasters; A Breathing Space for Independent Schools?; North to the Future; Quatercentenary Appeal; Major Events 1984; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address Changes; Golf; Rifle Club; Masonic Lodge; Notices; School Shop/Club Colours; Rugby Fixtures and Diary Dates; A Statistical History of Oakham School 1st XI Cricket; Centre Section - Oakham School Campus 1984. Eighteen double-pages A to R.

The Oakhamian Magazine, recording the Quatercentenary events throughout the year 1984. Contents: 1984 - A Personal View; A Backward Glance; Main Events; Summer Term Festivities; The Royal Visit; Other Opening Ceremonies.

This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

This file focusses on various publications, internal and external, under Tony Little's headmastership.

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 Old Oakhamian Magazines from 1980 to 1984.

This sub-series relates to weddings celebrated in the School Chapel over the years.

This sub-series contains various items relating to the Duke of Edinburgh's Award Scheme at Oakham School, for example licensing certificates.