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High school sport is one of the most popular school-based extracurricular activities in North America, situated as a developmental activity during which coaches can foster quality relationships with students to promote basic psychological needs satisfaction and teach life skills. The primary purpose of the study was to examine associations between coach–athlete relationships, basic psychological needs satisfaction and thwarting, and the teaching of life skills in Canadian high school sport. The secondary purpose consisted of addressing the psychometric properties of the scales employed in the study, namely the Coach–Athlete Relationship Questionnaire, the self-report version of the Interpersonal Behaviors Questionnaire, and a modified coach version of the Life Skills Scale for Sport. The sample was comprised of 1238 (58.8% male) Canadian high school coaches and the data were analysed using structural equation modelling. The mediated model indicated that coaches' perceptions of their interpersonal behaviours satisfying athletes' basic psychological needs either fully or partially mediated the positive relationships between coach–athlete relationships and the teaching of life skills. Coach–athlete relationships, particularly those within which coaches exhibit interpersonal behaviours that satisfy athletes' basic psychological needs, appear to be associated with the teaching of life skills in the context of high school sport.