A letter from the Headmaster G. Talbot Griffiths to teaching staff regarding the renaming of the forms in the School from Easter term 1956.

A letter from the Headmaster Henry Price to Parents reviewing the Winter term 2019. Contents: Inspection; Drama and Sports achievements; Form 7 reports.

A letter from the Headmaster Henry Price to Parents reviewing the Winter term 2020. Contents: Carol Services; Upper School reports; Drama Scholars' production.

A letter from the Headmaster Henry Price to Parents regarding staff changes in the Upper School in January 2021.

A headmaster's annual report for the academic year 1963-1964. Contents: Numbers; Staff; Activities; Health; Accommodation; Development Campaign; General. Attached is a report on the Sixth Form house (appendix A). Ten pages A to J.

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 1967, paying tribute to the Guest of Honour, Dr Hahn, discussing the Royal Visit, exam results and university successes, the Upper School innovations, shooting achievements, the Direct Grant and expansion of the School, K.R. Bowes's retirement. The speech is typed, with hand-written notations. Seven pages A to G.

A sermon given by Headmaster John Buchannan at the Leavers' Service 1958, relating to St Matthew 25, 29 and the parable of the talents. The sermon is typed, with hand-written notations. Eight pages A to H.

A newssheet from the Headmaster Richard Bull listing the achievements and events of the Spring term 1984.

A registrar's report for the year 1988, containing entry numbers, Sixth Form girls registration, and examination papers. Two pages A and B.