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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 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.

A letter from Anthony Earl to the Headmaster, Dr Joe Spence, regarding the passing of John Buchanan and sharing memories of him. Two pages A and B.

A letter from Judith Buchanan to the Headmaster, Dr Joe Spence, regarding the anniversary of the memorial service for her late father, John Buchanan, and thanking the School for remembering her father.

An invitation including a programme for a presentation on the International Baccalaureate and the Headmaster's Dinner on 11 October 2006.

A menu for the Headmaster's Dinner on 11 October 2006.

A press cutting announcing the nomination of Dr Joseph Spence as Headmaster of Oakham School, succeeding Mr Tony Little in 2002.

This series focusses on the headmastership of Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.

A menu for the Headmaster's Dinner on 25 February 2009.

Issue no.6 of 'Insight. The Magazine of HMC' published in June 2016, containing an article written by the Headmaster Nigel Lashbrook on Learning p.21 and an article written by former Headmaster Dr Joe Spence on Learning p.20.