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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

This file focusses on photographs of Tony Little, during his Headmastership (1996-2002).

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

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

A letter (A) from John Buchanan to Old Oakhamian thanking them for their generous retirement gifts and the O.O. London dinner, and addressing his farewells. Attached is a hand-written draft on the letter (B).

A sermon given by Headmaster John Buchannan at the Leavers' Service 1958, relating to St Matthew 25, 29 and the parable of the talents. The sermon is typed, with hand-written notations. Eight pages A to H.

A sermon given by Headmaster John Buchannan at the Leavers' Service 1961, relating to evil and positive teaching of Christian religion. The sermon is typed, with hand-written notations. Eight pages A to H.

A sermon given by Headmaster John Buchanan relating to St Matthew 7, 13. The sermon is typed, with hand-written notations. Seven pages A to G.

The Oakhamian Magazine, recording the Summer term 1967 (published in Winter term 1967). Contents: Editorial; School News; Avete; The Term now Standing; Music; Around the Societies; Face to Face; Travellers' Tales; Comment; Drama; Poetry; Games; The Combined Cadet Force; Shooting; Scouts; Letters to the Editor; O.O. News; University Entries; Valete.

The Oakhamian Magazine, recording the Winter term 1967 (published in Spring term 1968). Contents: Editorial; Term's Eye View; School News; Avete; Music; Around the Societies; Saas Fee; Around the Societies; Technology Projects; Face to Face; Opinion Poll; Features; We Pay our Respects to; Games; The Combined Cadet Force; Scouts; O.O. News; At the Universities; Letters to the Editor; Valete.