A letter from Geoffrey P. Lockwood to John Barber sharing memories on his time at school, prompted by an article in The Telegraph.

A letter from John Buchanan to Brian Welford congratulating him on the win against Uppingham and reflecting on Mr Welford's career as Rugby coach and the team's results.

A letter from Michael Stevens congratulating Brian Welford on the win against Uppingham.

A letter from Andrew to John Barber regarding his book "The Story of Oakham School" and sharing memories of his time at school as a pupil.

An internal note from the Headmaster Graham Smallbone to Teaching Staff regarding the Spring term 1988 reports.

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.

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 file focusses on Staff Burns Night organised by the Common Room. Most of the documents are letters and emails from 2006 and 2012.

This file focusses on the organisation of Staff Christmas parties in the late 2000s. Most of the file is made of email correspondence.