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.

Order of service for the service of thanksgiving to celebrate 50 years o marriage of Simon and Pip Schanschieff in the School Chapel on 21 September 2014.

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

This series relates to the History of Shooting at Oakham School. The collection is made of team photographs, score books and ephemera relating to successes at Bisley. The collection spans from the 1950s to 1980s.