OSSTF was first organized in this area, in 1920, as the Port Hope District OSSTF #9. The initial organization meeting was held in the Port Hope Library basement. During the meeting our first local President was elected, H.R.H. Kenner, the namesake for Kenner C.V.I. During this time, the District was subdivided into local councils; Peterborough, Lindsay, and Port Hope. It was also optional for teachers to be a part of the union. By 1940, 90% of all teachers in the area were Members, the second highest membership in the Province.
In 1968, school boards became to be based off of their counties, this created two districts in our area. In 1997, during the PC Harris government, this came quickly came to an end when school boards were amalgamated across the Province. With the amalgamation of Peterborough County Board of Education and the Northumberland-Clarington Board of Education our current District 14 came to be.