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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.

An almost complete collection of Oakham School magazines dating from 1884. Some editions are available as individuals whilst others can be found in larger bound volumes. There is also a collection of the Old Oakhamian magazine which is a separate school magazine for Old Oakhamians and their news.

This magazine covers all aspects of school life. Sporting, academic, and artistic achievements of the pupils are celebrated alongside news updates from various departments. In later issues, c. 1980s, houses are given space to announce news and in house achievements.

Sporting records are a key component of the magazine since its inception and there are accounts of matches (including scores and teams) in each edition. Again, since the 1980s, focus has shifted to also include all of the teams that compete for the school, instead of just focusing on the A team.

Images and photographs start to appear in the magazines from the 1970s and the magazine was first printed fully in colour in the 1990s.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

A bound copy of several Old Oakhamian Magazines from 1980 to 1984.

The Oakhamian Magazine, recording the Summer and Autumn terms 1981. Contents: Editorial; School News; Talbot Griffith; Religion; Prize winning Letter; Letters to the Editors; Profiles; Features; French Folies; Creative Writing; The Four Elements; Art & Design; Music; Drama; Societies; Ventures at Home & Abroad; Sport; University & Careers List.

The Oakhamian Magazine, recording the Summer and Winter terms 1983. Contents: Editorial; School News; Departures; Features; Now and Then; Expeditions; Excursions; Travel and Adventure; Music Reports; Drama Reports; Society Reports; Staff at Play; Art and Design Activities; C.C.F.; Duke of Edinburgh Award and Estate Management Activities; Sport; University and Careers List.

The Oakhamian Magazine, recording the Winter term 1985 and Spring term 1986. Contents: Editorial; School News; Charities and Community Service; Feature "Little Boxes"; Drama; Music; Societies; Adventures Abroad; C.C.F. and Duke of Edinburgh Award Activities; Sport.

A bound copy of several Old Oakhamian Magazines from 1985 to 1990.

The Oakhamian Magazine, recording the Spring and Summer terms 1985. Contents: Editorial; School News; Speech Day; Chapel; Careers & Business Studies Trips; The White Bix; Trips; Russia; Trinidad & Tobago; Australian Exchange; Drama; Blood Wedding; Hiawatha; The Cotchford Tales; Music; Societies; Art & Design Centre Activities; C.C.F. and DofE; Sport; Leavers' Destinations.