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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.

This collection highlights the depth and breadth of the school's curriculum and pupil's work. The drama and music sub-series are particularly detailed with their collection of production stills and programmes.

CUR/7 contains reports relating to the school's teaching and curriculum alongside timetables for lessons and exams, and comprehensive examination results for GCSE, A Level and IB.

Throughout the series in this collection, there is material relating to events and trips undertaken by various departments to increase the extra-curricular activities of pupils.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Summer term 2008. Contents: Staff News; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2008. Contents: Staff News; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

Order of service of the service of thanksgiving for Sheila Nicholson Hardy held at the School Chapel on 24 November 2013.

A book recording dates and times of services in the School Chapel, including the initials of the officiant, the attendance, the preacher, and the collections from Winter term 1991 to Spring term 2014.

A folder containing various documents on fundraising projects, the School's development plan; and examples of fundraising projects from other schools.

A small red book containing staff list, school list and school calendar for the Summer term 1982; hand-written notations. Item belonged to Jon Wills.

Two small red books (A and B) containing staff list, school list and school calendar for the Winter term 1995. Item A belonged to Mrs M. Frame and item B belonged to Mr Jon Wills. Both items have hand-written notations and amendments.

A small red book containing staff list, school list and school calendar for the Spring term 2009. Item belonged to Mr Jon Wills.