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Two similar photographs (A and B) of the Headmaster Tony Little and painter Binny Matthews at Speech Day 2002.

A letter from Michael Yeld to the Headmaster Tony Little regarding the donation of his father's, Robert Norman Yeld, drawing of Oakham School.

A letter from the Headmaster Tony Little to Parents regarding a review of the Spring term 2001. Contents: Sporting achievements; Debating; Arts, Music and Drama; Mobile Phones; Pubs, Clubs and Alcohol; Match Day Information; Summer term events.

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.

This file focusses on photographs and art work of Nigel Lashbrook, during his Headmastership (2009-2019).

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

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.

Notices compiled at the end of the Summer term 2018 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; School News; Parent Portal; School Archives; Art; Trustee Changes; Staff Changes. Three pages A to C.

Notices compiled at the end of the Winter term 2018 and sent to Parents. Contents: Director of Operation's Notices; Registrar's Notices; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; School Archives; Art; Staff Changes. Two pages A and B.

This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.