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 (r2 =.69). (author abstract)