In Canada, adolescent boys have been shown to have a higher high school dropout rate compared to girls. This situation is particularly evident in the country's second largest province by population, Quebec. The sport of Canadian football has recently gained in popularity in Quebec as many people believe that the sport can be used to promote both life skills and student engagement. The present study's purpose was to document coaches' and students' perspectives on student development through participation in high school football. Nine coaches and 18 students were interviewed through individual and focus group interviews and shared how they believe that students benefited personally and academically from playing high school football. Nevertheless, both coaches and students faced several challenges during the season that influenced the benefits students gained from their participation in sport. Findings suggest that high school sport, and more specifically high school football, can facilitate the positive development of students. However, to effectively promote student engagement, coaches must continually put in place strategies that help maintain students' motivation toward school.