A photograph of Andy Wolstenholme teaching a scrum. Date is unknown.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

Newspaper cuttings printed on one page reporting on the 1979 rugby visit from Japan School to Oakham School.

This sub-series focuses on various photographs of the Day boys in Johnsons House in the 1980s. Most of the collection is made of House sports teams.

A headmaster's annual report for the academic year 1984-1985. Contents: Some Thoughts on 1984/1985; Registrations/Entry Numbers; The Houses; Oakham Nursery School; Staff; General Academic; Examination Administration; University Entrance; Afternoon Activities; Sport Centre; Chapel; Food; Sanatorium; A.V.A. Centre; Careers Advice/ISCO Tests; Preparatory Schools Liaison/13+ Entry; Publicity/OSEL/Prospectus etc: The Queen Elizabeth Theatre; New Zealand Tour/Kenya Expedition; School Library; Old Oakhamian Club; House Names; Housemasters/Housemistresses; Conclusion. Attached are replies to a questionnaire for prospective parents (appendix A), some additional comments by Michael Stevens, a questionnaire for prospective parents, Overseas Universities Entries (appendix B), A-Level results (appendix C), O-Level results (appendix D), University entrance (Appendix F), a summary on Fastnet. Twenty-Seven pages A to AA.

A speech given by Headmaster John Buchanan on Speech Day 1965, paying tribute to the new Chairman, Thomas Haywood, discussing three innovations to the education at Oakham School - a small Sixth Form house, the building of a Technology Department, and the establishments of setting by subjects and tutors, and sporting achievements. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1972, paying tribute to Mr Eric Weiss who opened the new Sports Hall, discussing the Co-Education, sporting achievements and staff news. The speech is typed, with hand-written notations. Twelve pages A to L.

A list of pupils' names on three photographs: the 1984 Rugby team, the 1984 Chapmans house photograph and the 1985 Chapmans photograph.

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

This sub-file contains various photographs of Malcolm and Sheila Hardy, Housemaster of Wharflands.