This study examines the influence of both student and teacher perception of the student-teacher relationship on student’s attitude towards teachers and school. It also seeks to explore any gender differences in the perception of teacher-student relationship between male and female adolescents. A sample of 1,266 students (541 girls and 725 boys) from six different middle schools in Singapore participated in this study. Findings indicated that gender differences were observed for certain dimensions in the teacher-student relationship predicting their attitude towards teachers and school. Possible explanations for the obtained results were suggested and implications of the findings were also discussed.