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.

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.

A newspaper cutting from the Rutland Times of an article on Jim O'Kane, retiring after 33 years at Oakham School, and a photograph of the Lower School prizes winners at Speech Day.

A bound copy of several Oakhamian Magazines from 1884 to 1887. Inside the cover is a library sticker with the code 8JNX.

A bound copy of several Oakhamian Magazines from 1942 to 1948.

Oakham School Magazine, recording the Summer term 1890 (published in Winter term 1890). Contents: Speech Day; The Speech Day Sermon; Four Oakham men afloat; Newstead Abbey and Park; Western Australia; Poetry; Cricket; School Notes. Eleven double-pages A to K.

Oakham School Magazine, recording the Summer term 1891 (published in Winter term 1891). Contents: Editorial; School notes; Speech Day; The Brocken; Palmistry; Proverbs; Poetry; Old Oakhamian Club; Balance sheets; In Memoriam; Swimming Sports; Cricket; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1892 (published in Winter term 1892). Contents: Speech Day; School Notes; The Magillicuddy Reeks; Pilography; A Corner of Paris; Poetry; Cricket; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1897 (published in Winter term 1897). Contents: Editorial; School Notes; Old Oakhamian Club; In Memoriam; Prize Day; Cricket; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1924 (published in Winter term 1924). Contents: School Notes; Football Fixtures; O.T.C. Notes; The Annual Camp; Old Oakhamians' Quinquennial Meeting; Cricket. Five double-pages A to E.