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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 covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

This collection highlights the achievements of Old Oakhamians after they have left Oakham School.

This collection consists of the mainly the non-paper aspects of the archives collection. The collection is random in its make up but has a good material collection which highlights the changing nature of the school's uniform.

Items in this collection range in material type and stem from a variety of sources such as the Quatercentenary celebrations or items that were once used daily on the school grounds (such as building plaques or clock hands).

A bound copy of several Oakhamian Magazines from February 1988 to February 1991.

A bound copy of several Oakhamian Magazines from Summer 1993 to Summer 1997.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

The Old Oakhamian Magazine, published in October 1996. Contents: National 2 - RSC 2; O.O. Day 1996; Summer Holiday Success; Births, Engagements, Marriages & Deaths; Obituary; O.O. News; Lucy Pearson; Library; Lewis Moody; Chess.

The Oakhamian Magazine, recording the Spring term 1996. Contents: History; English; Performing Arts; C.C.F.; Science; Miscellany; Geography; Gap Year; Art; Sport; Houses; Miscellany.

The Old Oakhamian Magazine, published in Spring 1998. Contents: From the Headmaster; O.O. News; Births, Engagements, Marriages & Deaths; Obituaries; All Your Yesterdays; Oakham Memories; Sporting Highs; Oxford & Cambridge Places 1998.