Teacher-student relationships are beneficial for students and especially important in the middle school context. Suspensions are critical to reduce as it can be detrimental to the educational trajectory of students, particularly for marginalized students in underfunded schools. This study looked at the relations between teacher-student relationships and suspensions across the academic year in a sample of students (N = 541) and teachers (N = 51) in two urban school districts in the Midwest. A brief measure of teachers’ perceptions of relationships with students completed in the fall of the academic year predicted the odds of receiving in-school suspension (ISS; odds ratio [OR] = 0.65) and out-of-school suspension (OSS; OR = 0.72) by the end of the school year. Student reports of the relationships were also associated with ISS (OR = 0.94), but not OSS. On average, teachers’ report on the scale improved over the course of the school year (d = 0.11); however, student report of the relationships worsened (d = 0.30). The difference in the student report of the relationships from fall to spring was also associated with the odds of receiving ISS and OSS (ORs = 0.94). These findings suggest that student and teacher perceptions together are associated with harsh discipline practices that can negatively impact students developmental trajectories. Relationships can change but direct action is necessary to develop, maintain, and repair relationships during the academic year.