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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.

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 signed copy of "The Story of Oakham School" by John Barber. A book on the history of the school from its foundation in 1584, to celebrate the Quatercentenary. Preface written by Richard Bull, Headmaster. Some damage to cover.

Guidelines for Middle School Tutors, detailing their general responsibilities and their pastoral role at Oakham School. Two pages numbered A and B.

A copy of the Oakham School Red book, Winter 1979, owned by Terence Treanor. Notes and annotations on the inside.

A copy of the Oakham School Red book, Winter 1983, owned by Terence Treanor.

A copy of the Oakham School Red book, Winter 1978, owned by John L. Barber. Notes and annotations on the inside.

A copy of the Oakham School Red book, Winter 1981, owned by Terence Treanor. Notes and annotations on the inside.

A copy of the Oakham School Red book, Winter 1980, owned by Terence Treanor. Notes and annotations on the inside.

A copy of the Oakham School Red book, Winter 1977, owned by John L. Barber. Notes and annotations on the inside.