Research that uses self-report measures to examine the complexity of self-regulated learning (SRL) and academic challenges for adolescents is limited. This study examined the psychometric property of the Self-Regulated Learning Profile and Self-Diagnostic (SRL-PSD) instrument and addressed the multi-components of SRL and academic challenges for adolescents. Participants were 358 adolescents from a Canadian middle school. The subscales of SRL-PSD were administered to students through LimeSurvey during a 25-min instructional session over two days. Results demonstrated the SRL-PSD was a reliable and valid self-report instrument to measure adolescents' SRL practices and academic challenges. Also, all types of SRL practices and academic challenges were significantly intercorrelated. Additionally, all types of SRL practices were positively associated with school engagement, whereas all types of academic challenges were negatively associated with school engagement. Overall, this study provides a validated self-report measure for educators and researchers to examine adolescents' SRL practices and academic challenges.