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.

Reminiscences of Jim O'Kane on his time working at Oakham School between 1973 and 2006. Four pages A to D.

Two letter from Tony Earl congratulating John Barber on his book "The Story of Oakham School".

A press cuttings from the Kent and Sussex Courier regarding memories of W.L. Sargant and J. Story by OO Rev Gordon Clarke.

Oakham School Magazine, recording the Spring term 1890 (published in Summer term 1890). Contents: Early Rising; Four Months at Sea as an Apprentice; Jackdaws; Further Reminiscences of the late General Field; Poetry; The Athletic Sports; Entertainments; Debates; Library; Paperchases; Football; School Notes. Nine double-pages A to I.

Oakham School Magazine, recording the Spring term 1906 (published in Summer term 1906). Contents: Editorial; School Notes; Oakham School Sixty Years Ago; The Sports; Cricket; Correspondence.

An almost complete collection of Oakham School magazines dating from 1884. Some editions are available as individuals whilst others can be found in larger bound volumes. There is also a collection of the Old Oakhamian magazine which is a separate school magazine for Old Oakhamians and their news.

This magazine covers all aspects of school life. Sporting, academic, and artistic achievements of the pupils are celebrated alongside news updates from various departments. In later issues, c. 1980s, houses are given space to announce news and in house achievements.

Sporting records are a key component of the magazine since its inception and there are accounts of matches (including scores and teams) in each edition. Again, since the 1980s, focus has shifted to also include all of the teams that compete for the school, instead of just focusing on the A team.

Images and photographs start to appear in the magazines from the 1970s and the magazine was first printed fully in colour in the 1990s.

The Old Oakhamian Magazine, published in Autumn 2002. Contents: Letter from the Editors; Dr joe Spence - Headmaster; '87 Reunion; Tony Little; O.O. Families' Day; Louise Doughty; The First One; Births, Marriages & Deaths; Three OOs in a Boat; Stars, Stripes and OOs; All Our Yesterdays; Obituaries; News of; Sport.

This collection highlights the achievements of Old Oakhamians after they have left Oakham School.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.