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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 relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

Two lists of Commanding Officers and Officers of the O.T.C., J.T.C and C.C.F. since 1910, with names, ranks, and dates. Two pages A and B.

This file focusses on photographs of various Inspections of the Cadets and contingents, as well as group photographs of full contingents since the early 20th century.

This series focusses on various items relating to staff members which cannot be organised in any other series.

This series focusses on the history of the 21 Club at Oakham School.

This sub-series focusses on photographs of the boys in the 21 Club.

A book recording the Chapel's services including dates, hours, services, officiants and preachers, attendances and collections, from Winter term 1962 to Winter term 1977.

This sub-series focuses on photographs of the Junior Boarding boys of Sargants House. The collection is complete from 1966 to 2010, missing only the years 1970 and 2009.