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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.

This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

Issue no. 462 of The Rutland Times, Independence Souvenir Special, with reports on the celebration of the independence of Rutland. Thirteen double-pages A to M.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A photocopy of an obituary published in the Rutland Times, celebrating the lives of Gerald and Florence Botteley who passed away on the same day. Gerald Botteley was Head of Strings at Oakham School between 1969 to 1989.

This file focusses on obituaries and tributes written in memory of former Headmaster, John Buchanan, as well as letters from friends and family.

A photocopy of four obituaries and death notices published in local newspapers in 2005 after the death of former Headmaster John Buchanan.

This series focusses on obituaries, tributes and memorial services in memory of staff, teachers and their family.

A photocopy of a news paper article from The Rutland Times reporting on the European Chess finals to be held at Oakham School.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.