Background: Promoting good sportsmanship is a common goal of school physical education and many youth sport organizations. Teachers and coaches play a key role in accomplishing this goal. Thus, it is important to gather teachers’ and coaches’ reports of how they teach sportsmanship as well as youths’ perceptions of those behaviors to understand if and how this goal is being fulfilled. Purpose: To clarify the degree of alignment between leader and youth perceptions of sportsmanship by comparing: (a) physical education teachers’ self-reported sportsmanship teaching behaviors with their students’ perceptions of their teacher’s behavior and (b) youth sport coaches’ self-reported sportsmanship coaching behaviors with their athletes’ perceptions of their coach’s behaviors. Method: The physical education sample included 27 teachers and 837 boys and girls aged 11–15 years. The sport sample included 32 coaches and 246 boys and girls aged 10–15 years. Youth completed a survey about their leader’s behaviors related to sportsmanship. Leaders completed a parallel survey about their own behaviors. Results: Teachers rated themselves as significantly more often reinforcing and modeling good sportsmanship and punishing poor sportsmanship than students reported. Coaches rated themselves as significantly more often reinforcing and teaching good sportsmanship than perceived by their athletes. Conclusions: Misalignment between leaders’ and youths’ perceptions of several sportsmanship behaviors speaks to the importance of leaders engaging in strategies to accurately assess their own behaviors.