This series focusses on staff leavers, including list of staff changes, invitations to Leavers' events and booklets celebrating staff's time 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.

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 relates to staff leavers from 2006 to 2011, including lists of staff, farewell speeches and leavers' lunches.

This file focusses on letters received/sent by the Headmaster Nigel Lashbrook during his headmastership (2009-2019).

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

An invitation from Richard and Anne Bull to a farewell party in the Oakham Theatre foyer on 16 December 1984.

A letter from Clipsham tutors - Lick Brown, Steve Glynn, David Harrow, Frank Hayes, Ann Lewis and Peter Witchell - to parents asking them to contribute to a present for Mike and Margaret Rochester, retiring at the end of the academic year in 2004.

A letter from the Headmaster Nigel Lashbrook to Parents at the end of Summer term 2019, his last at Oakham School.

A letter from Dr John Doncaster to J.S. Padley regarding his son James going to College, and a memorandum on his School bill in the 1840s.