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 John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on various speeches given by John Buchannan during his headmastership and later. The bulk of the file is an almost complete collection of his Speech Day speeches.

A speech given by Headmaster John Buchanan on Speech Day 1961, paying tribute to the Guest, Chairman of a Bank, discussingimprovements to facilities, the Headmasters' Conference, boarding matters, exam results and overview of the past year at School. The speech is typed, with hand-written notations. Seven pages A to G.

A speech given by Headmaster John Buchanan on Speech Day 1963, paying tribute to the Guest, Professor Day-Lewis, discussing the Direct Grant and school fees, Education in Rutland, expansion in numbers and improved facilities. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1965, paying tribute to the new Chairman, Thomas Haywood, discussing three innovations to the education at Oakham School - a small Sixth Form house, the building of a Technology Department, and the establishments of setting by subjects and tutors, and sporting achievements. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1972, paying tribute to Mr Eric Weiss who opened the new Sports Hall, discussing the Co-Education, sporting achievements and staff news. The speech is typed, with hand-written notations. Twelve pages A to L.

A speech given by Headmaster John Buchanan on Speech Day addressing the boys, parents and staff. The speech is typed, with hand-written notations. Date is unknown, but estimated before co-education. Five pages A to E.

A speech given by Headmaster John Buchanan on Speech Day 1964, paying tribute to the late Chairman, Sir Eric Gore-Browne, discussing three reports on Education, examination results, Music and other activities, sporting achievements, boarding matters and the Development Campaign. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1969, discussing the changes in education in the country and the Direct Grant, and boarding matters. The speech is typed, with hand-written notations. Seven pages A to G.