It is well established that parental knowledge contributes to adolescents’ well-being and school success and scholars have noted that parents and adolescents report different levels of knowledge. Discrepancies in parental knowledge have implications for adolescent outcomes such as risk behaviors, but little is known about the implications of knowledge discrepancies for adolescents’ school outcomes. The present study examined discrepancies in parent and adolescent reports of parental knowledge and investigated the extent to which knowledge discrepancies were linked to school engagement. Participants were early adolescents (N = 174; 53 % female) and their parents (90 % mothers). Adolescents (57 % African American/Black, 18 % multiracial, 17 % White/Caucasian, 7 % Hispanic/Latino and 1 % Asian American) attended a Midwestern, Title 1, urban, public middle school. Adolescents completed surveys in their homerooms and parents completed paper–pencil surveys at home or surveys via telephone. Results showed that parents reported more knowledge of adolescents’ activities and whereabouts compared to adolescents’ reports. Knowledge discrepancies were associated with school bonding and school self-esteem such that dyads in which adolescents reported more knowledge than their parents reported had significantly higher levels of school bonding and school self-esteem compared to dyads in which parents reported much more knowledge.