Shame and guilt proneness are negative emotional dispositions that diverge in their behavioral responses. After a wrongdoing, shame tends to have a maladaptive influence on behavior, and guilt tends to have an adaptive influence on behavior. The current study sought to investigate shame and guilt tendencies among children and adolescents in a real-world context that has all the characteristics to generate these feelings: the hockey penalty box. We surveyed children and adolescent ice hockey players with experience serving time in the penalty box (N = 123). Findings showed that players who were higher in guilt proneness recalled experiencing more guilt-related feelings and cognitions in the penalty box than players lower in guilt proneness. The different cognitions relate to more anticipation of improving their playing. Players higher in shame proneness experienced more shame-related feelings and cognitions than players lower in shame proneness, which was related to more self-blaming. These findings have implications for the development and consequences of prosocial behaviors.