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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.

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

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

A calendar of events in the Winter term 1954. Three double-pages A to C.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2020-2021. Contents: The Headmaster Writes; News; New Faces; New Roles; Cover Story - Together Apart; Academic; Performing Arts; Trips and Activities; Community; Sport; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2002. Contents: Features; Old Oakhamians; Academic; Arts; Pastoral; Sport; Services.

The Oakhamian Magazine, recording the Winter term 1995. Contents: History; Science; English; Miscellany; Performing Arts; Art; Sport; Farewells; Music; Gap Years; Houses.

The Oakhamian Magazine, recording the Winter term 1998. Contents: Editorial; Chapel; Music; Drama; Art; Design & Technology; Short Stories; Trips; Now and Then; Sport Tour to South America; Sport; House Reports; Seventh Form Leavers '98.

Reminiscences of Jim O'Kane on his time working at Oakham School between 1973 and 2006. Four pages A to D.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.