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.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

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.

This sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2018 and Spring term 2019. Contents: Farewell to Headmaster Nigel Lashbrook; Academic; Performing Arts; Trips and Tours; Geography Trip to Morocco; Geography Trip to Iceland; Pastoral; Activities; Sport; Staff News; Old Oakhamian.

This file focusses on photographs and artwork of John Buchanan, during his Headmastership (1958-1977) and various visits to the School in the 1980s and 1990s.