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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.

The items in this series are books written and published by members of staff and are related to the history of Oakham School.

This focusses on research done on Rev Edward Vere Hodge's headmastership, in particular teaching and support staff working then, and life at Oakham School in the late 19th century.

This file focusses on admission prospectuses and various publications in the 1930s.

A speech given by Headmaster John Buchanan on Speech Day 1974, paying tribute to the Guest of Honour, the Provost of Derby, discussing the increase in numbers and co-education, the building programme, and the retirement of Jack and Betty Barber. The speech is typed, with hand-written notations. Six pages A to F.

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.

Jon Wills' school report in Winter term 1969.

Jon Wills' school report in Easter term 1970.

Jon Wills' school report in Winter term 1970.

Two photographs of the boys in Wharflands in the academic year 1965-1966 under the Housemaster John Barber. The photograph A is mounted on a card board and names are written on the back. The photograph A is slightly different.