The purpose of this study was to examine middle school students' recollections of their participation in a significant number of Sport Education seasons over a period of five years. Thirty-one (18 boys and 13 girls) eighth-grade students (average age at data collection = 13 years) who had all participated in at least 17 Sport Education seasons served as the participants in this study. Autobiographical memory theory guided qualitative data collection, which included surveys, formal interviews, focus group interviews, and autobiographical critical reflections. Student responses were categorized into general events, which had a focus on evaluating, preparation, first season, integrity, competition, and gamesmanship. Descriptive event-specific memories included authenticity and gameplay as most memorable aspects of students' experiences within multiple Sport Education seasons. The findings suggested that participating in multiple Sport Education seasons leads to better developed student roles and a stronger sense of fair play. More importantly, adherence to the central features of Sport Education and meaningful participation in several iterations of quality Sport Education seasons may be required for students to move closer to achieving the lofty goals of the model for students to become competent, literate, and enthusiastic sportspeople.