This study examined the direct and indirect associations of teachers' depressive symptoms with children's math achievement through teachers' reports of family-teacher relationships and children's approaches to learning (ATL) in Head Start. This study included 3- and 4-year-old 1,547 children (49% female; 27% White, 24% Black, 41% Hispanic/Latino, and 8% others) who attended Head Start from fall 2014 through spring 2015. Results indicated that teachers' depressive symptoms were directly associated with lower gains in children's math skills over a year. In addition, teachers who reported higher depressive symptoms were less likely to report positive family-teacher relationships. This, in turn, resulted in lower gains in children's ATL and was associated with lower achievement in math skills (r[superscript 2] = 0.69).