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 sub-file contains post cards related to the building and dedication of the War Memorial Chapel. Three post cards show the service of the laying of the foundation stone on Speech Day 1924. Four post cards show the dedication service on 29 October 1925. All post cards were published by Heawood & Son.

A blank post card showing the boys and staff gathered around the foundation stone on Speech Day in 1924, published by Heawood & Son, Melton Mowbray and Oakham.

A blank post card showing a procession leaving All Saints' Church on Speech Day in 1924, published by Heawood & Son, Melton Mowbray and Oakham.

A blank post card showing the Dr Theodore Woods, Bishop of Winchester, laying the foundation stone on Speech Day, in 1924. The post card was published by Heawood & Son, Melton Mowbray and Oakham.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This file focusses on various speeches given by John Buchanan during his headmastership and later. It is an almost complete collection of his sermons given at Oakham School since 1958.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).