We conducted three studies focusing on gender differences in the quality of student-teacher relationships (i.e., closeness and conflict) in the first 2 years of secondary education. Furthermore, we examined whether boys shared more favorable relationships with male teachers and whether girls shared more favorable relationships with female teachers (i.e., gender match hypothesis). Students (N = 812 in Study 1, N = 789 in Study 2, N = 484 in Study 3) reported about their relationship with their homeroom teacher (Study 1), Dutch and mathematics teachers (Study 2), or Dutch, mathematics, English, and history teachers (Study 3). Structural equation modeling revealed that, in six out of seven relationships, boys experienced more conflict with teachers than girls. In three out of seven relationships, boys also reported less closeness with teachers than girls. Teacher gender did not affect relationship quality, except for conflict with the homeroom teacher in Study 1 (i.e., students reported more conflict with female homeroom teachers than with male homeroom teachers). Finally, girls tended to experience more favorable relationships with female teachers than boys, partly supporting the gender match hypothesis. Thus, relationship-focused interventions in secondary education might benefit by accounting for gender match between students and teachers.