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A blue photo album containing photographs of the opening of Schanschieffs, retiring teachers, sports teams, the school orchestra, Oxbridge entrants, the 50th anniversary of Deanscroft/Haywoods, the Harvest Party, the Row Across Channel challenge, Sports Day and the visit of Garry Kasparov.

A speech given by Headmaster John Buchanan on Speech Day 1965, paying tribute to the new Chairman, Thomas Haywood, discussing three innovations to the education at Oakham School - a small Sixth Form house, the building of a Technology Department, and the establishments of setting by subjects and tutors, and sporting achievements. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1972, paying tribute to Mr Eric Weiss who opened the new Sports Hall, discussing the Co-Education, sporting achievements and staff news. The speech is typed, with hand-written notations. Twelve pages A to L.

Reminiscences of Jim O'Kane on his time working at Oakham School between 1973 and 2006. Four pages A to D.

A group of 430 slides taken by Jim Bride for the project "Sights and Sounds of Oakham School" between 1975 and 1976. Slides show staff and pupils in houses, on campus and in lessons, buildings, sporting events and other aspects of everyday life at school.

This series contains files of slides, taken at different time and by different creators, all showing the everyday life at Oakham School.

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.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2020-2021. Contents: The Headmaster Writes; News; New Faces; New Roles; Cover Story - Together Apart; Academic; Performing Arts; Trips and Activities; Community; Sport; Old Oakhamian.

The Oakhamian Magazine, recording the Winter term 1975. Contents: School News; Correspondence; Drama; The Chatty Catty Page; Jerwoods; Sport; Avete; Valete.

The Oakhamian Magazine, recording the Spring and Summer terms 1976. Contents: Editorial; School News; The School Council; Correspondence; Opinion; Societies; Music; Drama; The Chatty Catty Page; Jerwoods; Sport; R.A.F.; C.C.F.