The reporting of students' Learning Skills on the Ontario provincial report card provides educators and families with insight into students' work habits. However, the evaluation process is highly subjective. This study explores teachers' perceptions around student learning across demographic and institutional factors. This exploratory study is the first of its kind in Canada and draws data from the Toronto District School Board (TDSB), the nation's largest public board of education, serving approximately 246,000 students (2017-2018 data). Holding achievement as an independent variable, results indicate widespread differences in teachers' perceptions across student demographic identities and reveals significant implications on postsecondary access.