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This series focusses on the headmastership of Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.

Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

This file contains orders of services and programmes for the school's Carol Services over the years.

This sub-series relates to Carol services and other Christmas celebrations held in the School Chapel or in Peterborough Cathedral, over a period of several decades. The bulk of the sub-series focuses on the 2000s onwards.

This file contains orders of services for various weekly services attended by day pupils and boarders and Sunday services attended by the boarders.

This sub-series relates to Service programmes, focusing on Weekly and Sunday services, and services schedules and lists.

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.

Order of service of the service of thanksgiving for Jane Matthews at the School Chapel on 11 September 2012.

Order of service of the service of thanksgiving for Sheila Nicholson Hardy held at the School Chapel on 24 November 2013.

Order of service of the service of thanksgiving for the life of Dr John Cheverton held at the School Chapel on 25 March 2011.