This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

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 sub-series relates to the organisation of Lower School ski trip from 1998 to 2000.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

Two letters from the Headmsater, Graham Smallbone, to, respectively, Mr and Mrs Ham (A) and Mr and Mrs Wilkinson (B), related to Henrietta Lea's accident.

Typed letters from Lord Winchelsea to Georgiana mentioning a cricket match between Dr Doncaster's boys and the County, and a post-match dinner. Three pages A to C.

This sub-file focusses on letters sent by the Headmaster John Buchanan to Richard Walker (Head Boy, 1971) and his father, John Walker.

Two photocopies of notes from Nigel J. Sudborough and Richard Hill congratulating the Headmaster Dr Joe Spence on a successful day at the C.C.F. Biennial Inspection and Reunion on 5 May 2006. Two pages A and B.

This file focusses on obituaries and tributes written in memory of former Headmaster, John Buchanan, as well as letters from friends and family.

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.