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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

This file focusses on letters sent by Headmaster Richard Bull during his headmastership (1978-1984). The bulk of the collection is made of letters sent to Parents.

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 Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This file contains a selection of photographs informally taken of Seventh form girls during various events, including Speech Day, house photographs, fancy dress event.

Minutes of a Parent/Teacher Committee meeting held on 25 November 1978 at the Headmaster's house. Contents: Matters arising from the minutes; Careers; Speech Day and the end of the Summer term 1979; Any Other Business; Representation of the Committee; Date of the next meeting. Two pages A to B.

A calendar of events in the Summer term 1950. Three double-pages A to C.

A bound copy of several Oakhamian Magazines from 1884 to 1887. Inside the cover is a library sticker with the code 8JNX.

A bound copy of several Oakhamian Magazines from 1942 to 1948.

Oakham School Magazine, recording the Summer term 1890 (published in Winter term 1890). Contents: Speech Day; The Speech Day Sermon; Four Oakham men afloat; Newstead Abbey and Park; Western Australia; Poetry; Cricket; School Notes. Eleven double-pages A to K.