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 Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2012. Contents: Staff News; Trips and Tours; Features; Academic; Performing Arts; Pastoral; Community Activities; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine, recording the Summer term 1965 (published in Winter term 1965). Contents: School News; Avete; Term's Eye View; Drama; Music Notes; The Web; La Conférence Française; Societies; Opinion Poll; Literary; We Pay our Respects to; Proteus Weekend; Games; The Combined Cadet Force; Bisley - 1965; O.O. News; Correspondence; Valete.