Item consists of the September 1999 issue of The Whippet newsletter and includes articles about the purchase of the Cedar Croft Cabins and Cedar Croft Motor Court properties or six acres of land near East Field; academic structure at Appleby is modified with the creation of three 'schools': Middle School, Upper School and Senior School; United Way Week updates; prefects for 1999-2000 school year; and staff and faculty updates.

Item consists of the April 2000 edition of the Appleby Quarterly magazine. It includes articles on the official opening of Willis Hall, Appleby's first purpose built performance space, Appleby purchases the Cedar Croft cabin lands to add 2.4 hectare (six acres) of land to the College campus. It also includes an article about Appleby College hosting the Round Square conference, as well as changes to the academic structure including Campbell MacKay being appointed the schools first 'Associate Headmaster' and the creation of three 'schools' on campus: a Middle School, an Upper School and a Senior school. The terms 'Junior Year' and 'Senior Year' have been changed to 'Senior One' and 'Senior Two'.