This investigation examines teacher-student relationships among African American youth from low-income backgrounds (N = 193). Students and their teachers completed measures of teacher-student relationship quality and measures pertaining to emotional, behavioral, and school-related adjustment. Results indicated that African American youth who fell above the clinical cut point on the externalizing scale of the "Child Behavior Checklist" (n = 64) reported lower trust in relationships with teachers than did similarly matched students who did not have clinically significant externalizing symptomology. In addition, teachers rated students in the externalizing subgroup as lower in relational closeness and greater in relational conflict. Multiple regression analyses applied to data obtained from the behavioral risk group indicated that both student and teacher perceptions of teacher-student relationship quality were associated with student- and teacher-rated emotional, behavioral, and school-related adjustment. The strength of these associations varied as a function of data source and the specific relationship dimension investigated. Implications for future research and practice efforts aimed at building positive teacher-student relationships are discussed. (Contains 5 tables.)