A5 magazine, white cover with the badge of the school on the cover; 45 pages; contents listed on the inside cover: Editorial, This Year's President, Annual Dinner, Annual General Meeting and O.O. Day, Regional Meetings, School News, O.O. News, Engagements, Marriages, Births, Deaths, Obituaries, New Members, Changes of Address, Masonic Lodge, Notices, Diary Dates, Golf, Stop Press; with a portrait of G.R. Snailham, a photograph of the Opening of Jerwoods, a photograph of Jerwoods and pupils walking

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

A collection of documents relating to the Wilson Fields and cricket pavilion, including photographs of the opening. In 2005, the Springfield Playing Fields on Ashwell Road were renamed the Wilson Fields, to honour O.O. Lynn Wilson ('57). Lynn Wilson also funded the construction of a pavilion on the fields. The official opening ceremony took place on 16 May 2005.

A photograph of Mary Hoyle and her husband at the official opening of Stevens house, standing in front of the commemorative plaque on 18 October 1989.

A photograph of Lt Col Maxwell Heron ('74) inspecting Oakham School R.A.F. cadets in 1999 at the opening of the new C.C.F. Headquarters.

A photograph of Lt Col Maxwell Heron ('74) inspecting Oakham School R.A.F. cadets in 1999 at the opening of the new C.C.F. Headquarters.