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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.

A letter from the Headmaster Henry Price to Parents regarding the disruptions to External Examinations after the announcement of lockdown in the UK in March 2020.

This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2019-2020. Contents: The Headmaster Writes; Read All About It; News Faces; A Year in Pictures; A Coronavirus Challenge; Academic; Performing Arts; Trips and Tours; Community; Activities; Sport; Beyond Oakham; Old Oakhamian.

This sub-series relates to various services of baptism and confirmation held at the School Chapel. The largest file contains orders of service for Confirmation services.

A photograph of the Fifth Form girls going on a tutor outing to celebrate the end of the mock exams in January 2020. The girls were taken by their tutors, Mrs Helen Martin and Miss Aurore Guillomot-Bonnefond, to a restaurant in town and to escape rooms.

A photograph of some of the Sixth form girls in the garden for the House barbecue on the first weekend on the Winter term 2020.

The items in this sub-series are policies and guidance to staff and parents regarding Child Protection.

This file contains various items created by Richard Bull or relating to his headmastership (1977-1984).

A letter from the Headmaster Henry Price to Parents reviewing the Winter term 2020. Contents: Carol Services; Upper School reports; Drama Scholars' production.