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.

An invitation to the dinner including RSVP.

A5 magazine, green cover; 20 pages; contents listed on the cover: Editorial, The Old Oakhamian Club, Members of the Old Oakhamian Club 1898, Old Oakhamian Notes 1897-1898, The Old Oakhamian Dinner 1898, The Oakham School Register

A5 magazine, white cover with the badge of the school on the cover; 41 pages; contents listed on the inside cover: Editorial, This Year's President, Annual General Meeting, Annual Dinner, Regional Meetings, School News, O.O. Notes, Engagements, Births, Marriages, Deaths, Obituaries, New Members, Changes of Address, Review - "Shadow of the Eagle", Notices, Correspondence, Golf; with a portrait of W.L.S., a photograph of the Inspection of the C.C.F. by Lt.-General Sir Colin B. Callander

A5 magazine, white cover with the badge of the school on the cover; 44 pages; contents listed on the inside cover: Editorial, This Year's President, Annual General Meeting and O.O. Day, Annual Dinner, Regional Meetings, School News, O.O. News, R.F.D., Engagements, Marriages, Births, Deaths, Obituaries, New Members, Address List Part I, Masonic Lodge, Notices, Correspondence, Diary Dates, Seven-a-Sides, Golf; with a photograph of The Big Four, a photograph ofthe opening of the Technology Block

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

A5 magazine, white cover with the badge of the school on the cover; 48 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, L.J.C., A.J.E., A.J.E.J. and R.B.J., O.O. News, Engagements, Marriages, Births, Deaths, Obituaries, New Members, Changes of Address, Masonic Lodge, Notices, Diary Dates, Golf, Correspondence; with a portrait of T.K. Bullimore, a photograph of College House

A5 magazine, white cover with the badge of the school on the cover; 59 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, JW and HYH, O.O. News, Engagements, Marriages, Births, Deaths, Obituaries, New Members, Change of Address, Masonic Lodge, Notices, Diary Dates, Golf; with a portrait of J.G. Heron, a letter from Dr. Doncaster to the father of J.S. Padley