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 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.

Order of service for a service of celebration of the life of Peter James Witchell, Director of Music at Oakham School, in All Saints' Church on 27 October 2017.

Order of service for a memorial service for Dr john Cheverton, Head of Biology at Oakham School, in All Saints' Church on 15 October 2010.

Order of service for a memorial service for Philip Coates, Teacher of Music at Oakham School, in All Saints' Church, Thornage on 28 August 2014.

Order of service for a memorial service for Denis Giuseppi, Master of Shooting at Oakham School, in St Joseph's Roman Catholic Church on 21 December 2010.

This file contains an order of service and an obituary for Gerald Botteley, Head of Strings, and his wife Florence.

Order of service for the funeral service for Florence Ellen Botteley and Gerald William Botteley in the Parish Church of All Saints, Braunston, on 7 October 2021.

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.