Hope--a multidimensional positive motivational state--is particularly salient with adolescents in the school setting. Cognitive hope focuses on goal attainment cognitions whereas behavioral hope focuses on actions required for goal attainment. Studies rarely examine the contribution of each type of hope to adolescents' academic functioning and well-being. The present study examines the contributions of cognitive and behavioral hope to academic functioning (i.e., achievement and school engagement) and well-being (i.e., stress and anxiousness) across adolescence among 5th- through 12th-grade students (n = 643). When modeled concurrently, cognitive hope significantly predicted achievement, school engagement, anxiousness, and stress (high school only); however, aspects of behavioral hope only predicted school engagement. Findings provide evidence regarding the unique contribution of both types of hope in school settings and possible areas for intervention to foster hope in developmentally appropriate ways, depending on the age of the students and outcomes of interest.