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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.

The series contains negative files produced by Roger Blackmore, showing pupils, staff, school campus and buildings, drama productions, sports competitions and other activities.

A letter (A) from the Headmaster Graham Smallbone to be sent to Old Oakhamians after the Appeal launch. Attached are two lists (B and C) of recipients.

A photograph of Neil Mullinger, P.E. teacher, in 1994-1995.

A photograph of the guests, staff and former staff, attending the celebration of the 50 years of Deanscroft/Haywoods in 1998.

A programme for the Jerwoods Sports Day on 30 June 1999, including a list of events, the house teams, the 1998 results, the rules of competition and a list of the officials. Three double-pages A to C.

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

A programme for the memorial service of Lynn Wilson, containing a list of people involved in the organisation and a list of various tasks.

Email correspondence regarding the staff leavers' farewells in 2009, organised by the Common Room. Three pages A to C.

A headmaster's annual report for the academic year 1982-1983. Contents: Registrations/Entry/Numbers; The Houses; The Decem/Discipline; Staff; General Academic; The Academic Departments; Music; Art and Design; Drama; P.E. and Sport; C.C.F. and Duke of Edinburgh Award Scheme; Community Services; Afternoon Activities; Careers; Chaplaincy; The Ashburton Hall; Library; The Oakhamian; The School Council; Oakham School Nursery; Sanatorium; A.V.A. Centre; Postscript. Attached are A-Level results (appendix A), O-Level and A-Level results (appendix B), University Entrance (appendix C), a report to the Headmaster - Computing Department (appendix D). Thirteen pages A to M.