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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.

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 consists of a scrapbook of Appleby College material compiled by Bill Sefton. It includes correspondence from the Alumni Association about various fundraising initiatives, invitations to Alumni events, including the 50 year club, greeting cards, a report card from Easter 1932, John Bell Chapel service programs, correspondence with other alumni, Appleby College Old Boys Association membership cards, newspaper clippings about Hilda Chattaway include photographs of her grave and a letter explaining how to find the grave, invitation to the official opening of Colley House in 1990, newspaper clippings about Appleby events including the visit from Prince Andrew, the 1991 Tour of Appleby College choir to Europe, an article written by Bill about how he got his first job in 1937 at Loblaws and his career there. The scrapbook also includes 45 photographs (PH01-0135 - PH01-0178) of Appleby College and people associated with Appleby.

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.