His doctoral dissertation was on the Similarity of Hierarchically Organized Pairs of Pictures and Words as Reported by Field-Dependent and Field-Independent High-School Seniors.
In 1972 Winn started his academic career as assistant professor in the Department of Pedagogy, Faculty of Education, at the Université de Sherbrooke.
He was also director of the Learning Center at the Human Interface Technology Lab (HITLab), and adjunct professor in the College of Engineering, and the Music department.
In addition to teaching, extensive graduate advising activities, and a prolific writing schedule, at the time of his death he was working on research with the Puget Sound Marine Environment Modeling Group, augmented reality and physical models of complex organic molecules, INFACT/PixelMath, and collaborating with PRISM and the Center for Environmental Visualization.
For example, Winn explained “that the act of designing and creating environments that embody concepts and principles governing phenomena as diverse as wetlands ecology and medieval castles helps students master these topics with depth and clarity”.
Winn declared that this method of learning often result in misconceptions due to oversimplifying the interactions that occur in the natural environments which are simulated.
[3] One of the limitations of this study was that the students taking the “Virtual Puget Sound” (VPS) experience could only control some independent variables but not others, like for example they could not change the salinity of the water.
[3] After reading Winn's article titled "Current trends in educational technology research: The study of learning environments" published in 2002, the educational psychologist Richard Mayer (2003) criticized Winn's article for dismissing controlled experiments and in this way dismissing an approach that would produce substantial evidence and enable researchers to make claims on the learning development of students.
[4] As part of his response to Mayer's criticism, Winn articulates that a good non-experimental method for researchers to use is the “design experiment” which was described by Ann Brown in 1992.
[4] Winn made significant contributions[citation needed] to the field of educational technology as evident by his extensive research in this area.