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This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

A draft booklet produced by Captain R.M. Davies for the Centenary of the C.C.F. Contents: A Short Narrative History; Officers; SSIs and Helpers; Annual Camps; Inspecting Officers; Exams, Numbers and Training; Shooting; Band and Drums and parades. Twenty-two pages A to V.

Two notes from the Appeal Office to the Bursar (A) and the Headmaster (B), regarding the celebration of John Barber's birthday and the Barber Archive Room.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

A sermon given by Headmaster John Buchanan at a Junior Service in March 1977, relating to The Queen's Silver Jubilee. The sermon is typed, with hand-written notations. Six pages A to F.

A photograph of Lower School staff, including Joan Shorten, celebrating her 25th anniversary at Oakham School in February 1999.

A guest list for the celebration of the 50 years of Deanscroft/Haywoods. Guests include Old Oakhamians and the dates when they attended school, and staff. Two pages A and B.

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.

This sub-series contains various items relating to the Shooting team at Oakham School.