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An email from Jon Wills to all teaching staff regarding the history of Buggy Jerwood's oar and the 1908 London Olympics in which Jerwood competed. Rev F.H. Jerwood became the first Housemaster of Wharflands in 1920. There is also a list of five Old Oakhmian Olympians.

A letter from the Headmaster Tony Little to Parents regarding a review of the Winter term 2001. Contents: Achievements in Music and Drama; Debating; Sports; International Baccalaureate; Staff; Road Safety; E-mail; Next term.

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.

The Oakhamian Magazine, recording the Winter term 2001. Contents: Chapel; OSCA; Music and Drama; The Millennium Sculpture; Art; Design and Technology; Expeditions and Trips; Sport; House Reports.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Spring term 2006. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2010. Contents: Staff News; Features; Trips and Tours; Academic; Performing Arts; Pastoral; Community Activities; Sport; Foundation; Old Oakhamian.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2016. Contents: News; Features; Academic; Performing Arts; Trips and Tours; Cover Story; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation; The OO Interview.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2018. Contents: News; Cover Story; Speech Day 2018; Lower School Prize Giving 2018; Features; Performing Arts; Trips and Tours; Pastoral; Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian.

A booklet commemorating 30 years of Co-Education at Oakham School. Contents: message from John Buchanan, Up to 1970, the Concept of Co-Education, "There were a gallant lot", "For us, Co-Education is no an issue", "30 Years of Co-Education, highlights.