This paper describes the nature of home-school value discrepancies perceived by students, and tests associations between such value discrepancies and teacher-student relationships with student generational status as a moderator. Using a sample of 1,551 students from grades 10 and 11, chi-square tests and ANOVAs were used to describe the nature of discrepancies, while hierarchical linear regressions were conducted to test associations. Second-generation students generally perceived more differences between family-school values. When experiencing less value discrepancies, students reported closer teacher-student relationships. Value discrepancies were also associated with conflict, third-plus-generation standing out. Practitioners should mitigate value discrepancies to improve teacher-student relationships.