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Series consist of correspondence, newsletters, and holiday greetings sent by Appleby’s Old Boys’ Association (now Alumni) to Wentworth, and newspaper clippings about Appleby Old Boys’ events.

Series consist of correspondence from Appleby College to Wentworth regarding the progress of the school, Wentworth’s donation of the school bell, invitations to events, updates on Appleby alumni, educational viewpoints, and historical information. It includes typed and written letters as well as a telegraph.

Series consists of records pertaining to Alumni Relations, including Homecoming, 50-year Club, Alumni Directory, Reunion Dinners, Class Agent manuals. It also includes information on the Old Boys Alumni Association and Appleby College Alumni Association.

Series consists of records pertaining to students and employees who participated in World War 1 (one), gathered from student and employee files belonging to Appleby School. These files include Appleby School application forms, health records, letters between the school and parents regarding school fees, letters to Mr. Guest from students and employees enlisted and serving their country during World War 1. It also includes letters to Mr. Guest from parents and relatives of these individuals. The files are as follows: Aubrey Turquand, John Magee, Geoffrey Machell, Alex Gillespie, William Crawley, Sinclair Adams, Gordon King, Harward Chaffey, Osbert Calverley, Frank Griffin, John Laird, Andrew MacLean, Donald Macdonald, Vernon Powell, H.P. Rossiter, Ford Strathy, William Wright and Thomas Colley.

Series also includes copies of military files of students and employees who served. These files were printed from records available on Library and Archives Canada's website of World War 1 personnel.