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.

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

Obituary of John Buchanan published in Rutland Times, 11 August 2005, page 4.

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.

This file focusses on obituaries and tributes written in memory of former Headmaster, Richard Bull.

Announcement of the memorial service for Richard Bull in the Register section of The Times on 5 December 2015.

Announcement of the memorial service for Richard Bull in the Register section of The Daily Telegraph on 5 December 2015.

Order of service of the Thanksgiving service for the life of Oliver Richard Silvester Bull in Chapel on 23 January 2016.

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