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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.

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

This file focusses on invitations to various events under Henry Price's headmastership.

This sub-series focuses on various events organised by the girls of Gunthorpe house, in particular Charity events.

This sub-series contains various items relating to the Shooting team at Oakham School.

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.

Three letters from Rod Smith regarding arrangements for the Kasparov visit on 6 November 1997 and liaising with visiting prep schools for the day.

Chess puzzle from The Independent, with a short note on the start of Oakham School Junior International in 1992.

A newspaper cutting reporting on the start of the fifth International chess tournament at Oakham School in 1992.

A poster advertising a karaoke for Buchanans' and Rushebrookes' Sixth form girls in aid of JDRF for Type 1 diabetes research. The charity event was organised by Imogen Barton, Head of House.