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A newspaper cutting from the Rutland & Stamford Mercury reporting on the opening of BAFS cricket pavilion on 30 May 2014.

A menu for the Oakham School Rifle Club's Ashburton Celebration dinner on 6 December 1975.

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.

A newsletter from the Oakham School Foundation, 'Donum', issue no.1. Contents: 30 years of Co-Education, Three new Scholarships, Parent Fund, Legacies, Annual Giving "Investing in the Future", Old Oakhamian Parents' Society, International Receptions, Class of 2002, Message from the Chairman, From the Headmaster, 10 Year Development Plan, From the Foundation Director.

A letter from Alan Grieve to Roger Blackmore regarding paying for the Ball tickets and donating to the Appeal.

A letter from Roger Blackmore to Alan Grieve regarding future OSEL events.

A letter from Bryan Waites, Honorary Editor of the Rutland Record Society, to the Headmaster Graham Smallbone regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson and an article in This England.

A letter from Nicholas Bomford, Headmaster of Uppingham School to Bryan Waites regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.