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

Internal email correspondence regarding the organisation of the first Christmas Party in 2005, discussing matters such as date, menu, venue, guest list, costs, and entertainment. Thirty-nine pages A to AM.

Email correspondence relating to the organisation of the 2006 Staff Christmas party, including risk assessments, guests, hiring of music band, dancing and catering. Twenty-one pages A to U.

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

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.

Email correspondence regarding the staff leavers' farewells in 2009, organised by the Common Room. Three pages A to C.

A complete collection of Red Books - School lists and Calendars since 1959. Red books give information regarding pupils, tutor groups, teaching and support staff, school calendar and events, school rules, future trips and dates. Only two Red Books were never published, Summer term 2020 and Spring term 2021 as the UK was in lockdown (COVID-19) and pupils were not at School and had lessons online.

This subfonds contains the Archive's complete collection of Red books. These books contain a calendar of events for the upcoming term, lists of pupils and their houses, and lists of staff.

This collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.