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 collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

Order of service (A) for a memorial service for Sir David John Davenport-Handley in All Saints' Church on 25 March 2014; and a blank card to record names of attendees (B).

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

This sub-series focuses on the service of dedication of the pulpit in memory of former Headmaster Rev Edward Vere Hodge in 1934.

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

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

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, John Buchanan, as well as letters from friends and family.