A blue photo album containing photographs of the opening of Schanschieffs, retiring teachers, sports teams, the school orchestra, Oxbridge entrants, the 50th anniversary of Deanscroft/Haywoods, the Harvest Party, the Row Across Channel challenge, Sports Day and the visit of Garry Kasparov.

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 certificate from the Diana Princess of Wales Memorial Award for Young People in recognition of students who have made a real difference to tackling bullying in their school communities awarded to Jerwoods Film Activity in the academic year 2005-2006.

An email from Charles Welch to the Jerwood Housemasters regarding the results of Jerwoods interhouse competitions during the summer term, ahead of the Jerwoods Presentations in Assembly on 30 June 2004.

A War Certificate 'A' awarded to cadet Anthony Jeffrey Doy of the Oakham School Contingent J.T.C. on 21 March 1945.

A Certificate 'A' awarded to cadet Philip Gordon Pearce-Smith of the Oakham School Contingent C.C.F. on 21 March 1949.

This file contains various items created by Richard Bull or relating to his headmastership (1977-1984).

A book (A) by Bryan Matthews, 'The Book of Rutland', given to Nigel Straton as a formal present for the Nelson Firth prize, awarded at Speech Day 1980 by the Headmaster Richard Bull. Enclosed is a letter (B) from Richard Bull to Nigel Straton; and a letter (C) from R.M. Chillery to the School, who found the book in a charity shop.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A War Certificate "A" awarded on 24 April 1944 to Cadet John David Witter who passed the examination on 21 March 1944.