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This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

A letter (A) from John Buchanan to Old Oakhamian thanking them for their generous retirement gifts and the O.O. London dinner, and addressing his farewells. Attached is a hand-written draft on the letter (B).

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

A letter (A) from Graham Smallbone, Headmaster, Simon Schanschieff, Chairman of Trustees, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, to former pupils who were at Oakham during John Barber's years with the School regarding celebrating his eightieth birthday and the Barber Archives. Attached is a reply slip (B).

This sub-series focuses on letters related to the history of Wharflands house, its pupils and staff.

Nine letters between Graham Smallbone, Bryan Waites, Stephen Garnett and Nicholas Bomford regarding the 450th anniversary of the birth of Archdeacon Robert Johnson.

Two letters, from Trevor Case and Roger Blackmore to John Barber regarding the sums produced by the sales of signed copies of "The Story of Oakham School" to the Quatercentenary Appeal.

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.

Notes from John Barber to Michael Stevens regarding the celebrations of the 450th anniversary of the birth of Archdeacon Robert Johnson.

A collection related to the History of Oakham School since its foundation, including research on Headmasters, Masters and pupils, and articles and books published by Headmasters and teachers.