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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.

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 copy of the portrait of Headmaster Nigel Lashbrook, painted by O.O. Rebecca Haley ('17). The original painting was presented on his last Speech Day.

A letter from the Headmaster Nigel Lashbrook to Parents at the end of the Winter term 2018. Contents: Parent/Teacher Committee; Teaching & Learning; Website and School Portals; Sustainability.

A policy on the aims of Oakham School, written by the Headmaster Nigel Lashbrook in 2018. Two pages A and B.

Notices compiled at the end of the Summer term 2018 and sent to Parents. Contents: Change of status requests; Form 3 Registrations; Siblings enquiring for Form 6 entry; Non EEA pupils; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; School News; Parent Portal; School Archives; Art; Trustee Changes; Staff Changes. Three pages A to C.

Notices compiled at the end of the Winter term 2018 and sent to Parents. Contents: Director of Operation's Notices; Registrar's Notices; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; School Archives; Art; Staff Changes. Two pages A and B.

The items are Red Books and one Leavers' Handbook accumulated by Rev. Terence Treanor over the years.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2009 and Spring term 2010. Contents: Features; Staff News; Trips and Tours; Academic; Performing Arts; Pastoral; Community Activities; Sport; Beyond Oakham; Foundation; Old Oakhamian.