A certificate from the Diana Princess of Wales Memorial Award for Young People in recognition of students who have made a real difference to tackling bullying in their school communities awarded to Jerwoods Film Activity in the academic year 2005-2006.

Certificate A awarded to Philip Gordon Pearce-Smith. Poor condition

A War Certificate A awarded to Anthony Jeffrey Doy

A framed certificate rewarding Oakham School working to change the lives of formerly homeless people

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 history book entitled "The book of Rutland", given by Headmaster ORS Bull to Nigel Staton as a formal present for the Nelson Firth Prize. Donated by RM Chillery. Enclosing a letter from Bull and a letter from donor Chillery. Items A to C

An email from Charles Welch to the Jerwood Housemasters regarding the results of Jerwoods interhouse competitions during the summer term, ahead of the Jerwoods Presentations in Assembly on 30 June 2004.

A blue photo album of Oakhamians and visitors: Schanschieff's Opening; Little, Alan Duncan MP, Wiliam Hague MP, Tom Lazur, Poppy Moore, Lord Sebastian Coe, Graham Lee, Martin Johnson, Ben Wheeler, Roger Blackmore, Philip Coates, Sheila Hardy, Jane Matthews, Margaret Cousins, Gary Kasparov, Pert, David Garner, Daniel Hyde, Matthew Pilling, Nicholas Branston, sports teams, pupils, a play