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.

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

Copy of a French-Canadian newspaper article reporting on Lesiège-Svidler match at Oakham School Junior International in 1992.

A letter from Rod Smith regarding the list of prep schools coming to Oakham School for the visit of Garry Kasparov in November 1997.

An invoice from Alton Towers for Oakham School visit's to the amusement park on 21 May 2000.

A poster advertising an Oakham School Medical Society event with Old Oakhamians discussing Medicine careers held in the Wilson Auditorium on 23 March 2022.

A menu for a dinner in the Barraclough on 18 November 1988.

Press cuttings from local and international newspapers reporting on the Oakham School Junior Chess tournament in 1992.

Newspaper cutting reporting on the first round of the Oakham School Junior International in 1992.

Newspaper cutting reporting on the second round of Oakham School Junior International in 1992.