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 file contains photographs owned by Rev Terence Treanor on various topics: House photographs, Sports team and school events and dinners.

A photograph of an Old Oakhamian dinner in the House of Lords, London.

Old Oakhamian Calendar, published in 1921. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1920; Letter from the Headmaster with plan; Old Oakhamian Notes; Old Boys' Matches. Six double-pages A to F.

Old Oakhamian Calendar, published in 1899. Cover with contents: Editorial; The Old Oakhamian Club; Members of the Old Oakhamian Club - 1898; Old Oakhamian Notes; The Old Oakhamian Dinner - 1898; The Oakham School Register. This is the first issue of the Old Oakhamian Magazine, recording news of the O.O. Club and former pupils.

The Old Oakhamian Magazine, published in 1956. Contents: Editorial; Annual General Meeting; Annual Dinner; Regional Meetings; Old Oakhamian Fund; Opening of the War Memorial Library; School News; O.O. Notes; Medals of Father Douglass; John Haywood; Engagements; Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Notices; Golf. Nine double-pages A to I.

The Old Oakhamian Magazine, published in 1959. Contents: Editorial; This Year's President; Annual General Meeting; Annual Dinner; Regional Meetings; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Changes of Address; Book Review; Notices; Golf. Eleven double-pages A to K.

The Old Oakhamian Magazine, Sargant In Memoriam number, published in 1957. Contents: 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. Twelve double-pages A to L.

The Old Oakhamian Magazine, published in 1961. Contents: Editorial; This Year's President; Annual General Meeting; Annual Dinner; Regional Meetings; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part I; Notices; Golf; Stop Press. Twelve double-pages A to L.

The Old Oakhamian Magazine, published in 1958. Contents: Editorial; This Year's President; Annual General Meeting; Annual Dinner; Regional Meetings; O.O. Fund; G.T.G.; School News; O.O. Notes; 19th Century School; Engagements, Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Notices; Golf. Ten double-pages A to J.