Understanding how social support and anxiety influence academic engagement in boys and girls is important to ensure that we effectively promote academic engagement. This study examined the relationship between gender, social support, anxiety, and academic engagement in elementary and junior high school students. Students in Grades 5 to 9 (N = 1,904) completed self-reports measuring academic engagement, anxiety, and perceived social support from family, friends, and school staff. Results indicated that girls were more likely to perceive social support and to score higher on the anxiety scale than boys were. Grade level was a significant predictor of academic engagement for boys but not for girls, while anxiety classification was a significant predictor of academic engagement for girls but not for boys. This study highlights the importance of understanding the multiple factors that influence academic engagement to provide targeted prevention and intervention strategies and how these factors differ for boys and girls.