This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

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).

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.

Order of service for a service of thanksgiving for Thomas Charles Stanley Haywood, Chairman of Trustees, at All Saints' Church on 21 February 2003.

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.

Order of service for a memorial service for Ian Hugh Stuart Balfour, Clerk to the Bursar at Oakham School, in All Saints' Church on 30 May 2012.

Order of service for a memorial service for The Right Reverend Ian Cundy, Bishop of Peterborough, in Peterborough Cathedral on 19 May 2009.

Order of service for a memorial service for Walter Howard Wainwright in All Saints' Church on 25 November 2016.

This file focusses on the Memorial Service for Brian Primmer, Director of Music (1950-1959), and includes letters from Old Oakhamians.

Order of service for a service of remembrance for Bob Burchnall, teacher at Oakham School, in St Edmund's Church, Egleton, on 13 December 2017.