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A5 magazine with a photograph of Old School under the snow on the cover; 89 pages; contents: Our First Lady President, Annual Dinner, O.O. Day and A.G.M.'s, Regional Reunions, School News - Round-up, O.S.E.L., O.S.C.A., Oakham Festival Week, Music, Drama, C.C.F., Duke of Edinburgh's Award Scheme, O.S.E.S., Sport, New Members, Address Changes, Engagements, Marriages, Births, Deaths, Obituaries, O.O. News, Letters, Nostalgia, O.O. Golf Society, O.O. Rifle Club, O.O. Lodge, Club Colours/School Shop, Notices, Diary Dates, Rugby Fixtures; with a portrait of Virginia Measures, various photographs of the O.O. Golf Society on the back cover

A4 magazine, stapled; 8 pages; a portrait of the new Headmaster Tony Little on the cover; contents: O.O. Day 1996, O.O. Shooting, Obituary, Orations, Announcements, O.O. News, Sport

A5 magazine, white cover with the badge of the school on the cover; 56 pages; contents listed on the inside cover: 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; with a portrait of P.I.D. James, a photograph of the O.O. Golfing Society

A5 magazine, white cover with the badge of the school on the cover; 54 pages; contents listed on the inside cover: Editorial, This Year's President, Annual Dinner, Annual General Meeting and O.O. Day, Regional Meetings, School News, J.L.D. and M.D., O.O. News, Engagements, Marriages, Births, Deaths, Obituaries, New Members, Address List Part IV, Masonic Lodge, Notices, Diary Dates, Golf; with a portrait of B.A.F. Smith, a portrait of Father Louis Merton; with 3 loose documents: a Rutland Memorial Hospital Appeal, addresses of some O.O. missing and an invitation to Old Boys' Day on 14/06/1969

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.

1 menu from the dinner signed by Garry Kasparov. Inside one menu is a typed, paper version. Items A and B

A photograph of guests before the Chess dinner in honour of Garry Kasparov on 6 November 1997.