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The sub-series focuses on the Humfrey Family, more particularly on Stuart and Douglas Humfrey, and include "The Humf Letters".

This series focusses on recreational events for staff by the Common Room and by Oakham School Enterprise Ltd, such as Christmas Parties, Burns Night and swimming pool sessions, from 2005.

This sub-series is made of various items, such as informal photographs of the girls in Ancaster, house events, house prefects and miscellaneous objects. The bulk of the sub-series focuses on the 2000s.

This sub-series focuses on the rededication of the War Memorial Chapel in 2007. The refurbishment of the Chapel was largely due to the generosity of O.O. Brian A.F. Smith ('54). The service coincided with the opening of Littles house, an extension of Roun House, the Seventh Form girls' house.

This sub-series relates to Carol services and other Christmas celebrations held in the School Chapel or in Peterborough Cathedral, over a period of several decades. The bulk of the sub-series focuses on the 2000s onwards.

This sub-series contains books used by pupils during services in chapel or books published by staff or Old Oakhamians and given to the school. A large part of this sub-series contains hymns books compiled by Rev T.C.H. Clare ('29).

This sub-series focuses on Seventh Form Leavers' service held in Chapel. The bulk of the sub-series is orders of services.

A collection of documents relating to the Wilson Fields and cricket pavilion, including photographs of the opening. In 2005, the Springfield Playing Fields on Ashwell Road were renamed the Wilson Fields, to honour O.O. Lynn Wilson ('57). Lynn Wilson also funded the construction of a pavilion on the fields. The official opening ceremony took place on 16 May 2005.