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This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This file focusses on letters sent/received by G. Talbot Griffith.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

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.

An almost complete collection of the School's magazines dating from 1884.

Oakham School Magazine, recording the Spring term 1928 (published in Summer term 1928). Contents: School Notes; O.O. Club Notes; The Chapel Fund; Fives; The Sports; Sidney Sussex Run; Boxing and Fencing Club; O.T.C.; The School Register; To G.H.; Friday Music; Lectures; Cambridge Letter; Cricket; Correspondence; Games Balance Sheet. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1928 (published in Winter term 1928). Contents: Editorial; School Notes; Speech Day; A Discontented Classic; Cricket; Informal Concert; O.T.C.; Mytchett Farm Camp 1928; O.O. Notes; Correspondence; Library; Acknowledgements. Nine double-pages A to I.

Oakham School Magazine, recording the Winter term 1928 (published in Spring term 1929). Contents: Frontispiece; Editorial; School Notes; The Concert; The Lamp of Life; The Prison Doors; Football; O.T.C.; The School Register; The Debating Society; O.O. News. The name 'T. Worthington' is hand-written on the cover. Eight double-pages A to H.

Oakham School Magazine, recording the Summer term 1929 (published in Winter term 1929). Contents: Editorial; School Notes; Speech Day; Resignation of Mr Sargant; End of Term; Reynard's Night Hunt; Cricket; O.T.C.; O.O. News. Eight double-pages A to H.

Oakham School Magazine, recording the Winter term 1929 (published in Spring term 1930). It is the 46th year of the Magazine. Contents: Frontispiece; Editorial; School Notes; School Concert; Wind in the Trees; Two Country Squires in the Shires; Lectures; Football; The Steeplechases; O.T.C.; O.O. News; Correspondence. The name 'Worthington' is hand-written on the cover. Eight double-pages A to H.