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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 collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

Two letters, from Trevor Case and Roger Blackmore to John Barber regarding the sums produced by the sales of signed copies of "The Story of Oakham School" to the Quatercentenary Appeal.

A letter from Robert Fellowes, in service to the Queen at Buckingham Palace, to Richard Bull thanking the Headmaster, the school staff and pupils on behalf of The Queen and The Duke of Edinburgh for the visit and the celebrations of the Quatercentenary, and thanking John Barber for a copy of his book "The Story of Oakham School".

A letter from Major A.A. Greenwood congratulating John Barber on his book "The Story of Oakham School" and attaching an index of printing errors.

A copy of the Oakham School Red book, Winter 1984, owned by Terence Treanor.

A press cuttings from the Kent and Sussex Courier regarding memories of W.L. Sargant and J. Story by OO Rev Gordon Clarke.

A press cutting from the Nottingham Evening Post regarding the publication of "The Story of Oakham School" by John Barber to celebrate the Quatercentenary of the school and the connections with Nottingham.

A letter from John Barber asking for permission to use a photograph of Rev Edward Vere Hodge in his upcoming publication.

A letter from Ian Reid congratulating John Barber on his book "The Story of Oakham" and regarding the upcoming Quatercentenary celebrations.