This paper examines child and teacher reports of school adjustment. Of interest is the match, or mismatch, between children’s perceptions of themselves and their feelings about school, and the classroom teachers’ ratings of their school-related problem behaviours and competencies. The effects of child gender and age of starting school were also considered. Data included children’s self-rated cognitive and physical abilities and acceptance by peers, school liking and avoidance and feelings about their teachers, and descriptions of what they liked about school. Teachers provided ratings of children’s adjustment problems (acting out, shy/anxious, learning difficulties) and competencies (task orientation, frustration tolerance, confidence in class, peer social skills). Analyses showed little effect of age, but a significant effect of gender. Girls were more positive about school, and teachers rated boys as having more problems of adjustment. Comparative analyses of relations between child- and teacher-reported adjustment also showed gender differences. Boys who liked school and their teachers had better learning and social strengths, and fewer behaviour problems. Girls who said they enjoyed schoolwork activities had higher ratings on school competencies. Counter-intuitively, perceived social acceptance by peers and enjoyment of social play (for girls) were negatively correlated with teachers’ ratings of school adjustment. Implications for teachers’ expectations of adjustment and gender are discussed.