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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 Gregory congratulating John Barber on his book "The Story of Oakham School" and asking to be credited for his photograph.

A letter from Simon congratulating John Barber on his book "The Story of Oakham School".

A letter from Bob Price congratulating John Barber on his book "The Story of Oakham School".

A letter from C. Gordon F. Clark sending to John Barber a cutting from the Kent and Sussex Courier regarding the publication of "The Story of Oakham School".

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 Frederick H.G. Percy, Honorary Archivist of Whitgift School, to John Barber, regarding old School Houses in various school and enclosing his research on Schoolhouses' dimensions in English schools.

A letter from Moira thanking John Barber for sending a form to purchase his book "The Story of Oakham School".

A letter from David Tew thanking John Barber for sending a copy of his book "The Story of Oakham School".

A letter from Mark Jenkins to John Barber, prompted by an article in the Rutland Journal advertising the publication of "The Story of Oakham School" and sharing memories of the digging of the Roman Villa at Great Casterton while at school.