The current study explored the relationships between three components of gender identity, peer support, math anxiety, and math outcomes in a sample of middle school students (*N* = 295). Separate path analyses were conducted for girls and boys. For boys, gender contentedness was related to higher math grades through a reduction in evaluation math anxiety. For girls, felt pressure was related to a reduction in self reported math grades through an increase in learning math anxiety. In addition, peer support in math was associated with lower learning math anxiety and higher math grades for girls, whereas peer support in math was not associated with math anxiety or math outcomes for boys. Implications for future research and education interventions are discussed.