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This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

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 focusses on programmes, invitations and menus to various events under Dr Joe Spence's headmastership.

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

An invitation and reply form to the Headmaster's Dinner on 11 October 2006.

An invitation including a programme for a presentation on the International Baccalaureate and the Headmaster's Dinner on 11 October 2006.

A menu for the Headmaster's Dinner on 11 October 2006.

A menu for the Headmaster's Dinner on 25 February 2009.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.