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This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

This sub-series focusses on photographs of Oakham School 1st Shooting VIII, mostly during the 1950s and 1960s, as well as teams competing in the Ashburton Competition at Bisley.

This series relates to the History of Shooting at Oakham School. The collection is made of team photographs, score books and ephemera relating to successes at Bisley. The collection spans from the 1950s to 1980s.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

Three letters from Alan Grieve and Roger Blackmore regarding OSEL events and Activity Holidays in 1984 and the need to add to the catering staff.

A group of four letters relating to a proposal for a 'Careers in Medicine' video, a project proposed by John Metcalfe at The Royal Society of Medicine.

Two letters between Roger Blackmore and Alan Grieve on various matters, such as the last OSEL meeting, the new brochure for the Medical Congress and OSEL accounts.

Two letters between Roger Blackmore and Alan Grieve relating to a board meeting on 10 July 1984.

A letter (A) from Roger Blackmore to Alan Grieve regarding the booking for the Activity Holidays and inviting the Trustees' wives. Attached is a letter (B) from Alan Grieve to the Trustees' wives inviting them to take part in the Activity Holidays in the summer.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.