A letter addressed to John Barber referring to the last paragraph in his book "The Story of Oakham School" on pp.74-75 and regarding the purchase on Doncaster Close and the 1932 Reform Act.

A prospectus promoting studying at Oakham School in 1902. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

A prospectus promoting studying at Oakham School in 1903, with illustrations. Contents: Brief History; Subjects of Instruction; Boarding Houses; Health; Games; Holidays.

A prospectus promoting studying at Oakham School in the 1930s. Contents: Staff; Admission; Work; Fees; Optional Payments; Absence & Remission of Fees; Health; Entrance Scholarships; Other Scholarships & Exhibitions; Buildings; Boarding Houses; Holidays & Hours; Games & Hobbies; School Societies; Expenses; Clothes List.

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 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.

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 note from the Headmaster Tony Little regarding the history of the school, its location, academic performance and co-curricular activities, sports, and school life.

A newspaper article reporting on Oakham School winning against Southend School to reach the quarter finals of the 2002 National School's Chess championship.