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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 series focusses on staff leavers, including list of staff changes, invitations to Leavers' events and booklets celebrating staff's time at Oakham School

A letter from the Headmaster Nigel Lashbrook to Parents at the end of Spring term 2019. Contents: Examinations; Gala Concert; Decem; Brexit.

Notices compiled at the end of the Winter term 2017 and sent to Parents. Contents: Change of status requests; Form 3 Registrations; Siblings enquiring for Form 6 entry; Non EEA pupils; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; Parent Portal; School Archives; Art; Staff Changes. Two pages A and B.

A letter from the Headmaster Nigel Lashbrook to Parents at the end of Summer term 2019, his last at Oakham School.

A letter from the Headmaster Nigel Lashbrook to Greg Andrews regarding John Buchanan's letter to his friend Edward Leigh.

This file relates to staff leavers from 2006 to 2011, including lists of staff, farewell speeches and leavers' lunches.

Three letters between Adam Lowe and Jon Wills related to the Kilburn Road Gaol, now the Richard Bull Centre, and visiting College House and the School Archives.

This file focusses on letters received/sent by the Headmaster Nigel Lashbrook during his headmastership (2009-2019).

Letters between the Headmaster Nigel Lashbrook and former teacher Greg Andrews regarding John Buchanan's letter to his friend Edward Leigh.