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.

A5 magazine named The Oakhamian, stappled; 24 pages; contents on the inside cover: Long Live the King, Editorial, School Notes, Music Notes, Entertainment, Debating Society, O.T.C., Scouts, Cricket, Swimming Sports, Football, O.O. News, Scholarships to the United States, Acknowledgements; with a drawing for Sargant's 70th birthday

A yellow notebook recording the performance of candidates who took the entrance examination in 1977.

A red notebook with lists of names for Junior Entry, including the waiting list and the registration, from January 1959 to 1989.

A newsletter from the Oakham School Foundation, 'Donum', issue no.1. Contents: 30 years of Co-Education, Three new Scholarships, Parent Fund, Legacies, Annual Giving "Investing in the Future", Old Oakhamian Parents' Society, International Receptions, Class of 2002, Message from the Chairman, From the Headmaster, 10 Year Development Plan, From the Foundation Director.

A letter from the Headmaster Graham Smallbone to Parents on the term: reports, scholars, examinations, appointments, school accounts, insurance, music fees, activity holidays, games, Chap 86 Appeal and OSCA

A prospectus for the school including names of trustees and staff, information on the school, boarding, the library, societies, terms, holidays, health, scholarships and prizes. Items A to C

Information on scholarships at a variety of institutions like Eton and how this affects Oakham. Items A to H

A paper on gifted teachers and the recruiting of them. Items A to G