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 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 Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

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 letter from Bob to John Barber regarding Tom Badgery's letter and the purchase of Doncaster Close and the 1832 Reform Act.

A letter from Roger Blackmore to Alan Grieve regarding the 1985-1986 programme of activities and events organised by OSEL. Two pages A and B.

A letter from Pat Johnson, Senior Mistress of Sevenoaks School, regarding the H.M.C. Co-Educational Schools meeting of Senior Mistresses at Sevenoaks School on 9 November 1989, including directions, the programme of the day and a map of Sevenoaks School. Two pages numbered A and B.

A letter from Michelle Northcott, Housemistress of Lincoln House, to Parents and Guardians reviewing the 2017 Winter term's achievements and events.

A letter from K.R. Bowes to T.W. Badgery regarding the purchase of Doncaster Close and the 1832 Reform Bill abolishing the Rotten Boroughs. The letter was enclosed with HIS/1/2/4/48.

A letter from Iain Simpson, Director of Sports, inviting Parents and Guardians to attend a talk on positive parenting and helping children through adolescent years.