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A seating plan for the H.M. Armed Forces reunion lunch on 5 May 2006, with some hand-written amendments.

An invitation and reply form to the Headmaster's Dinner on 11 October 2006.

A folder containing various documents on fundraising projects, the School's development plan; and examples of fundraising projects from other schools.

A collection of invitation and programme for the C.C.F. Biennial Inspection on 5 May 2006, as well as correspondence from the Foundation to guests, and letters from guests to the School regarding the event.

Two letters (A and B) between Jeremy Tomlinson, Bursar & Clerk to the Trustees, and Philip Robson at Daltons Solicitors, regarding the estate of the late John David Buchanan.

Four letters sent/ received by Joe Spence and Paul Spicer regarding the composition of 'A Living Stone' and the arrangements for the Rededication service in 2007.

This series focuses on various dedication and rededication services since the opening of the School Chapel. Most items are orders of services.

A newsletter from the Oakham School Foundation, 'Donum', issue no.1. Contents: 30 years of Co-Education, Three new Scholarships, Parent Fund, Legacies, Annual Giving "Investing in the Future", Old Oakhamian Parents' Society, International Receptions, Class of 2002, Message from the Chairman, From the Headmaster, 10 Year Development Plan, From the Foundation Director.

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

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.