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This collection focuses on major events that have occurred to the school and its pupils. This includes the Quatercentenary celebrations and the school's reaction to the COVID-19 pandemic.

The Quatercentenary celebrations compromised of several events including the visit to the school by Queen Elizabeth II and Prince Philip, Quatercentenary ball, and special productions to celebrate the recent opening of the Queen Elizabeth Theatre.

There is a detailed series on the school's Speech Day which includes a comprehensive list of programmes and award winners from the ceremony.

There is a excellent record of items showing how the school reacted to the COVID-19 pandemic. There is general communication to parents and staff, information on the structure of face to face and distance learning teaching, and also an illuminating collection of photographs taken by Ms. Fernandez in 2021.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A headmaster's annual report for the academic year 1965-1966. Contents: Numbers; Staff; Activities; Health; Accommodation; Old Oakhamians; Circular 10/65; General. Attached are A-Level results (appendix A) and a report on conference 'Life in Industry' (appendix B). Thirteen pages A to M.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2019-2020. Contents: The Headmaster Writes; Read All About It; News Faces; A Year in Pictures; A Coronavirus Challenge; Academic; Performing Arts; Trips and Tours; Community; Activities; Sport; Beyond Oakham; Old Oakhamian.

The Old Oakhamian Magazine, published in 1980. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address Changes; Masonic Lodge; Notices; Diary Dates; Rugby Fixtures; Golf; Rifle Club; Letters; R.G.H.; Stop Press. Fifteen double-pages A to O.

The Old Oakhamian Magazine, published in 1983. Contents: The Story Of Oakham School; Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; Oakham to Close?; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address Changes; Golf; Rifle Club; Masonic Lodge; Notices; Club Colours; Rugby Fixtures; Diary Dates. Twenty-one double-pages A to U.

A bound copy of several Oakhamian Magazines from Spring 1972 to Summer 1976.

Photo albums and scrapbooks compiled by members of staff throughout the years.

The Old Oakhamian Magazine, published in 1988. Contents: 1888 And All That; O.O. Club 1888-1988 - Presidents and Hon. Secretaries; This Year's President; Annual Dinner; O.O. Day and A.G.M.; Regional Reunions; School News - Round-up; Tributes to the retiring Staff - MS, AV, PW, MB; Today's Sixth Former; The Barraclough; O.S.E.L.; O.S.C.A.; Chapel; Music; Drama; C.C.F.; Duke of Edinburgh's Award Scheme; O.S.E.S.; Sport; O.O. News; New Members; Address Changes; Engagements, Marriages, Births & Deaths; Obituaries; Oakham's Art Masters; The Oldest Old Oakhamian?; O.O. Golfing Society; O.O. Rifle Club; O.O. Lodge; Club Colours/School Shop; Notices; Diary Dates; Rugby Fixtures; Yes, I Remember it Well! (Answers). Twenty-four double-pages A to X.

A bound copy of several Old Oakhamian Magazines from 1985 to 1990.