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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

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.

Newspaper cutting from The Grantham Journal, reporting on the 1929 Speech Day and W.L. Sargant's retirement. Includes a detailed list of Honours and Prizes.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

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 calendar of events in the Summer term 1950. Three double-pages A to C.

Minutes of a Parent/Teacher Committee meeting held on 25 November 1978 at the Headmaster's house. Contents: Matters arising from the minutes; Careers; Speech Day and the end of the Summer term 1979; Any Other Business; Representation of the Committee; Date of the next meeting. Two pages A to B.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This file focusses on letters sent by Headmaster Richard Bull during his headmastership (1978-1984). The bulk of the collection is made of letters sent to Parents.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.