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

A video tape (22 minutes) produced by Geoffrey Isles Photography, containing William Winter's photographs taken between 1950 and 1955. William Winter was a Resident Tutor in Wharflands and a teacher of English and History.

A monograph written by Brian Needham recording the School Rugby 1st XV statistics and its history, from 1892 to 2012.

A group of negatives used as the illustrations in "The Story of Oakham School".

Oakham School Magazine, recording the Winter term 1898 (published in Spring term 1899). Contents: The Concerts; School Notes; Paperchase; Down a Coal-Mine; Some Legends and Customs of the Maori; Football; Correspondence. Eight double-pages A to H.

Oakham School Magazine, recording the Summer term 1901 (published in Winter term 1901). Contents: Editorial; School Notes; Speech Day; Football; Cricket. Seven double-pages A to G.

Oakham School Magazine, recording the Winter term 1893 (published in Spring term 1894). Contents: The Concerts; School Notes; Top Hats; A Visit to a Coal Mine; A Tour on Wheels and off them; Haddon Hall; Poetry; The Origin of Rugby Football; Football; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Winter term 1894 (published in Spring term 1895). Contents: Frontispiece; Editorial; School Notes; The Concerts; In Memoriam; The Gymnasium; Some Experiences of the Slums of London; Football; Correspondence. The first page is a photograph of the Rugby 1st XV 1894-1895. Eight double-pages A to H.

Oakham School Magazine, recording the Winter term 1895 (published in Spring term 1896). Contents: Editorial; School Notes; Gymnasium; Football "Nines"; The Concerts; Old Oakhamian Club; Staffa and Iona; A Carnival at Carlsruhe; Football; Correspondence. Seven double-pages A to G.

Oakham School Magazine, recording the Winter term 1896 (published in Spring term 1897). Contents: Editorial; School Notes; Gymnasium; Concert; Old Boys' Club; Beards; Football; Correspondence. Seven double-pages A to G.