This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

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

Old Oakhamian Calendar, published in 1899. Cover with contents: Editorial; The Old Oakhamian Club; Members of the Old Oakhamian Club - 1898; Old Oakhamian Notes; The Old Oakhamian Dinner - 1898; The Oakham School Register. This is the first issue of the Old Oakhamian Magazine, recording news of the O.O. Club and former pupils.

Old Oakhamian Calendar, published in 1921. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1920; Letter from the Headmaster with plan; Old Oakhamian Notes; Old Boys' Matches. Six double-pages A to F.

The Old Oakhamian Magazine, Sargant In Memoriam number, published in 1957. Contents: Editorial; This Year's President; Annual General Meeting; Annual Dinner; Regional Meetings; School News; O.O. Notes; Engagements, Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Review - Shadow of the Eagle; Notices; Correspondence; Golf. Twelve double-pages A to L.

The Old Oakhamian Magazine, published in 1956. Contents: Editorial; Annual General Meeting; Annual Dinner; Regional Meetings; Old Oakhamian Fund; Opening of the War Memorial Library; School News; O.O. Notes; Medals of Father Douglass; John Haywood; Engagements; Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Notices; Golf. Nine double-pages A to I.

The Old Oakhamian Magazine, published in 1959. Contents: Editorial; This Year's President; Annual General Meeting; Annual Dinner; Regional Meetings; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Changes of Address; Book Review; Notices; Golf. Eleven double-pages A to K.

The Old Oakhamian Magazine, published in 1968. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; O.O. News; K.R.B.; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part III; Masonic Lodge; Notices; Diary Dates; Golf. Fourteen double-pages A to N.

The Old Oakhamian Magazine, published in 1971. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; T.C.M.R.; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List; Masonic Lodge; Notices; Diary Dates; Golf. Eleven double-pages A to K.

The Old Oakhamian Magazine, published in 1972. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; Gordon Purdy; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Changes of Address; Masonic Lodge; Notices; Diary Dates; Golf. Fourteen double-pages A to N.