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A5 magazine, red cover with the badge of the school on the cover; 85 pages; contents listed inside: 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, J.D.B.'s "An Oakham Overture to Poetry", Centre Section - Oakham School Campus 1985; with photographs of the Royal Visit, portraits of Graham Smallbone, S.G. Schanschieff, a photograph of 5 old masters; with a loose document:a programme of the Old Oakhamian Day 08/06/1985; bottom o page 77 has been cut off

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.

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

A complete collection of Red Books - School lists and Calendars since 1959. Red books give information regarding pupils, tutor groups, teaching and support staff, school calendar and events, school rules, future trips and dates. Only two Red Books were never published, Summer term 2020 and Spring term 2021 as the UK was in lockdown (COVID-19) and pupils were not at School and had lessons online.